Coumaranedione-3-monoximes

Details Coumaranedione-3-monoximes Coumaranedione-3-monoximes

1974-08-08

1976-11-23

Patten, James A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424279, C07D49300

Patent

active

039936660

ABSTRACT:
Coumaranedione-3-monoximes which may be substituted in the benzene ring by halo or alkyl. The compounds are obtained by treating the corresponding 2-hydroxyphenylacetic acid lactone with nitrous acid or with an ester, salt or chloride of nitrous acid in an acid medium. The coumaranedione-3-monoxime thus obtained is an intermediate which undergoes hydrogenation in the presence of a suitable acid anhydride to afford the corresponding 3-amidocoumaranone, which compound, upon hydrolysis in the presence of dilute acid, affords the corresponding .alpha.-amino-2-hydroxyphenylacetic acid. That product is also an intermediate which has utility in the synthesis of antibiotics, including cephalosporin and penicillin derivatives.

REFERENCES:
patent: 2473484 (1949-06-01), Ullyot
Wislicenus et al., Ber. v. 42, (1909), pp. 1930-1940.

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