2-(5-Chloro-7-nitroindolin-1-yl)benzamide → 2-(5-Chloro-7-aminoindolin-1-yl)benzamide

HRID 34307Notes

Reaction equation

HRID 34307 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-])=O)[CH:10]=1)[N:7]([C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17])[CH2:6][CH2:5]2>CN(C)C=O.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH2:11])[CH:10]=1)[N:7]([C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17])[CH2:6][CH2:5]2

Participants

4

Reactant 1

HCID 138233492-(5-Chloro-7-nitroindolin-1-yl)benzamide

Product 1

HCID 138232702-(5-Chloro-7-aminoindolin-1-yl)benzamideYield 119.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To this solution of 2-(5-chloro-7-nitroindolin-1-yl)benzamide of Example 1b (10 gm, 26.5 mmoles) in dimethylformamide (DMF) [100 ml] and ethanol (100 ml) was added 1% Pt/carbon (2.0 gm). The mixture was shaken under hydrogen (59 psi) for 41/2 hours. The mixture was then filtered under nitrogen and concentrated to remove solvent at 55° C. and high vacuum to give a solid (9.1 gm). Recrystallization from chloroform twice afforded 2-(5-chloro-7-aminoindolin-1-yl)benzamide, (4.3 gm, 47.3%), m.p. 199°-201° C. dec.

Workup

  1. filtrationThe mixture was then filtered under nitrogen
  2. concentrationconcentrated
  3. customto remove solvent at 55° C.

Sources & evidence

ORD record
ord-b0f9f697a4884bd489d214abea7167af
Source dataset
uspto-grants-1988_08
Patent number
US04761411

Reaction notes

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