Potassium Carbonate → HCID 59300847, compound

HRID 2235351Notes

Reaction equation

HRID 2235351 reaction equation
[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH:11]C(=O)C)[CH:9]=2)[NH:4][C:3]1=[O:18].[CH3:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25](Br)[CH:24]=1)=[O:22].C([O-])([O-])=O.[K+].[K+]>>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[N:4]([CH2:20][C:21](=[O:22])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 165023'-BromoacetophenoneHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300847HCID 59300847, compoundYield 82.4%

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (8 g) is alkylated using 3-bromoacetophenone (6.8 g; 33.4 mmol) and K2CO3 (11.3 g; 82 mmol) at RT for 3 h. After filtration and evaporation of the solvent the crude material is de-acetylated under reflux conditions in 2-propanol (111 ml) and hydrochloric acid (6 N; 75 ml). Pure 5-amino-3,3-dimethyl-6-nitro-1-(2-oxo-2-phenyl-ethyl)-1,3-dihydro-indol-2-one (8.5 g) is obtained by aqueous work-up and re-crystallization.

Workup

  1. customat RT
  2. customfor 3 h
  3. filtrationAfter filtration and evaporation of the solvent the crude material

Sources & evidence

ORD record
ord-8d7d63f28f034abe86aa28e1cd55b8ba
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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