5-Chloro-indole preparation

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

548490, 548491, C07D20908

Patent

active

043776990

ABSTRACT:
An improved process for the preparation of 5-chloro-indole comprising reacting indoline in a chlorine-inert organic solvent with an acylating agent of an organic carboxylic acid to obtain the corresponding 1-acyl-indoline, reacting the latter in the presence of water and a basic agent with chlorine to form 5-chloro-1-acyl-indoline, subjecting the latter to saponification to obtain 5-chloro-indoline and reacting the latter in a water-immiscible organic solvent by heating with an aromatic nitrocompound in the presence of a finely powdered ruthenium catalyst to form 5-chloro-indole in excellent yields.

REFERENCES:
patent: 3184466 (1965-05-01), Hennig et al.
patent: 4005206 (1977-01-01), Gaignault et al.
Mazza et al. (Farmaco, Ed. Sci., vol. 32 (1) (1977), p. 54.
Japanese Patent Appln. Serial No. 77,108,969 filed in 1977 [Chem. Abs., vol. 88 (1978), p. 136451x].
Huisgen et al., [Chem. Ber., vol. 93 (1960), p. 1496-1506].
Ikan et al. [Israel J. Chem., vol. 2 (2) (1964), p. 37-42].
Thesing et al. [Chem. Ber., vol. 95(1962), p. 2205].
Gall et al., [J. Org. Chem., vol. 20 (1955), p. 1538].
British Patent 919,864 [Chem. Abstracts, vol. 59, (1963), Col. 8710].
Japanese Patent Appln. 69-27967 [Chem. Abstracts vol. 72, (1970), p. 43446d].
Terent'ev et al., [Proc. Acad. Sci. USSR, vol. 118(2) (1958), p. 49-52].
French Patent 1,576,807 [Chem. Abs. vol. 72(1970), p. 121360n].
Bader et al., [J.A.C.S., vol. 83 (1961), p. 3319].
Hunt et al. , [J. Chem. Soc., (C) (1966), p. 344-345].
Bakke [Acta, Chem. Scand., vol. 28(1974) No. 1, p. 134].
Imai et al., [Org. Chem., vol. 42(3) (1977), p. 431].
Imai et al., [Chemistry Letters, (1976), p. 855-856, 655-656].

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

5-Chloro-indole preparation does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 5-Chloro-indole preparation, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 5-Chloro-indole preparation will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1870257

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.