Process for producing 2-(2-hydroxymethylphenyl)acetamide derivat

Details Process for producing 2-(2-hydroxymethylphenyl)acetamide derivat Process for producing 2-(2-hydroxymethylphenyl)acetamide derivat

1997-06-10

1999-01-05

Kumar, Shailendra

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

549 28, 549 65, 549417, 549419, 549475, 556465, 556482, 564162, 564163, 564164, 564165, 562840, 562843, C07C23305

Patent

active

058565736

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP95/02621 filed Dec. 21, 1995.


FIELD OF THE INVENTION

The present invention relates to a process for producing a 2-(2-hydroxymethylphenyl)acetamide derivative, particularly a 2-(2-hydroxymethylphenyl)-2-alkoxy(or hydroxy)iminoacetamide, which is an intermediate for the production of alkoxyiminoacetamide compounds useful as agricultural fungicides. The present invention also relates to an intermediate for the production of the 2-(2-hydroxymethylphenyl)acetamide derivative.


BACKGROUND OF THE INVENTION

A 2-(2-hydroxymethylphenyl)-2-alkoxy(or hydroxy)-iminoacetamide is an important intermediate for the production of alkoxyiminoacetamide derivatives useful as agricultural fungicides (see JP-A 3-246268, JP-A 4-182461). The following processes for producing the intermediate are known: the process comprising reacting a 2-(2-halomethylphenyl)-2-alkoxyiminoacetic acid ester with a metal acetate, followed by an amine (JP-A 3-246268), and the process comprising converting the halomethyl group of a 2-(2-halomethylphenyl)-2-alkoxyiminoacetamide to a hydroxymethyl group (JP-A 5-097768).
However, there is still room for improvement in these processes.
The object of the present invention is to provide an industrially advantageous process for producing a 2-(2-hydroxymethylphenyl)-2-alkoxy(or hydroxy)iminoacetamide.
Another object of the present invention is to provide an intermediate for the production of a 2-(2-hydroxymethylphenyl)-2-alkoxy(or hydroxy)iminoacetamide.


DISCLOSURE OF THE INVENTION

The present inventors have intensively researched to achieve the above objects. As a result, it has been found that a 2-(2-hydroxymethylphenyl)-2-alkoxy(or hydroxy)iminoacetamide can be obtained by subjecting the corresponding compound in which the hydroxyl group of the hydroxymethyl group is protected to deprotection. Thus, the present invention has been accomplished.
The present invention relates to a process for producing a compound of the formula (I): ##STR3## wherein R.sup.1 and R.sup.2 are the same or different and are hydrogen or alkyl, and R is hydrogen or alkyl, which comprises removing the protective group (P) of hydroxyl of a compound of the formula (II): ##STR4## wherein P is a protective group of hydroxyl, .about. indicates an E-isomer, Z-isomer or a mixture thereof, and the other symbols are as defined above.
In a preferred aspect, the present invention relates to a process for producing a compound of the formula (I-2): ##STR5## wherein R.sup.3 is alkyl and the other symbols are as defined above, which comprises removing a protective group (P) of hydroxyl of a compound of the formula (II-1): ##STR6## wherein each symbol is as defined above, to obtain a compound of the formula (I-1): ##STR7## wherein each symbol is as defined above, and then alkylating the compound of the formula (I-1).
In the present invention, the compound of the formula (II) can be obtained by reacting a compound of the formula (IV): ##STR8## wherein each symbol is as defined above, with a compound of the formula (III):
The present invention also provides a compound of the formula (II'): ##STR9## wherein R.sup.1 and R.sup.2 are the same or different and are hydrogen or alkyl, R is hydrogen or alkyl, P.sup.2 is aralkyl, trialkylsilyl, triaralkylsilyl, alkyldiarylsilyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydrofuranyl, tetrahydrothiofuranyl or aralkyloxyalkyl, and .about. indicates an E-isomer, Z-isomer or a mixture thereof; and a compound of the formula (IV'): ##STR10## wherein each symbol is as defined above (The compounds of the formulas (II') and (IV') are included in the above formulas (II) and (IV), respectively).
The alkyl represented by R, R.sup.1, R.sup.2 and R.sup.3 in the above formulas includes, for example, alkyl having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isobutyl, sec-butyl, t-butyl, etc. In particular, methyl is preferred.
The protective groups of hydroxyl represented by P and P.sup.2 inclu

REFERENCES:
patent: 5387714 (1995-02-01), Takase et al.
patent: 5414122 (1995-05-01), Murabayashi et al.

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