Hydrochloric Acid → 6-Amino-1-ethyl-3,3-dimethyl-5-nitro-1,3-dihydro-indol-2-one

HRID 2374478Notes

Reaction equation

HRID 2374478 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([N+:16]([O-:18])=[O:17])=[C:9]([NH:12]C(=O)C)[CH:10]=2)[C:5]([CH3:20])([CH3:19])[C:4]1=[O:21])[CH3:2].Cl>C(O)C>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6]([C:5]([CH3:19])([CH3:20])[C:4](=[O:21])[N:3]2[CH2:1][CH3:2])=[CH:7][C:8]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69070578N-(1-ethyl-3,3-dimethyl-5-nitro-2-oxo-2,3-dihydro-1H-indol-6-yl)-acetamide

Product 1

HCID 690705916-Amino-1-ethyl-3,3-dimethyl-5-nitro-1,3-dihydro-indol-2-oneYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(1-ethyl-3,3-dimethyl-5-nitro-2-oxo-2,3-dihydro-1H-indol-6-yl)-acetamide (5.2 g, 17.85 mmol) was dissolved in ethanol (40 ml). After addition of hydrochloric acid (25%, 8 ml, 81.44 mmol) the mixture was stirred under reflux for 3 h. The reaction mixture was allowed to cool down to room temperature and then quenched with water (80 ml). The yellow precipitate was isolated by suction and washed with ethanol/water (1:1). The solid was dissolved in ethyl acetate, dried over sodium sulfate and concentrated to yield 4.15 g (93%) 6-amino-1-ethyl-3,3-dimethyl-5-nitro-1,3-dihydro-indol-2-one as a orange solid.

Workup

  1. temperatureunder reflux for 3 h
  2. customquenched with water (80 ml)
  3. customThe yellow precipitate was isolated by suction
  4. washwashed with ethanol/water (1:1)
  5. dissolutionThe solid was dissolved in ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2d652f3cb9b14207ad762a38d3bed11a
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

Loading…