PROCEDE POUR LA PREPARATION DES DERIVES D'INDOLINE

• Main Authors: VERN,GORDON,DECRIES,US, DANIEL,BRYAN M.,US, RUDDY,LITTELL,US, ALLEN,RODGER,US, MCEVOY,JOSEPH,US
• Format: Patent
• Language: French
• Published: 15.11.1978
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

1382917 1-Acylindolines AMERICAN CYANAMID CO 3 May 1972 [27 May 1971] 56237/73 Divided out of 1382916 Heading C2C The invention comprises compounds of formula where R 1 is H, Cl, Br, C 1-4 alkoxy, NO 2 , NH 2 , AcNH or NMe 2 , and R 2 is H, C 1-4 alkoxy or NO 2 , or R 1 R 2 is -OCH 2 O-; R 3 is H or Me; Y is PhCO (possibly substituted by Cl or NO 2 ) or C 2-4 alkanoyl; and Z is OH, Cl, Br, MeSO 3 or p-TsO. In examples, these compounds are prepared by (a) acylating the corresponding N- unsubstituted compounds (and if necessary saponifying an initial compound where Z = (e.g.) OAc); (b) introducing an NO 2 group by nitration and if appropriate reducing to NH 2 ; (c) converting Z = OH to the other values for Z; (d) (for Z = OH) reducing a corresponding indoline-3-acetic acid or its ester, or its mixed anhydride with EEOCO 2 H. Intermediates otherwise prepared have the formulae RH, 3-R:C(OH)CO 2 Et, 3-RCH 2 CO 2 Et, [R being a 2-oxoindoline residue, substituted by 5,6-(MeO) 2 or 5,6-(OCH 2 O)], R0CH 2 CO 2 CO 2 Et (R0 = 2-oxomdolin-3-yl), R*CH 2 CO 2 Et (R* = 5 - methoxy - 2 - methyl- or 5,6 - dimethoxy -2 - methyl - indolin - 3 - yl, or 5,6 - dimethoxy - 2- methylindol - 3 - yl), and XCH 2 CO 2 H [X = 5-nitrobenzodioxol (1,3) - 6 - yl (and Me ester) and the 5-amino analogue (Me ester)].