Potassium Carbonate → HCID 59300852, compound

HRID 2235368Notes

Reaction equation

HRID 2235368 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].Br[CH2:21][C:22](=[O:25])[CH2:23][CH3:24].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]([CH2:21][C:22](=[O:25])[CH2:23][CH3:24])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 131561-Bromo-2-butanoneHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300852HCID 59300852, compoundYield 25.8%

Procedure

Analogously to the general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (2 g) is alkylated using 1-bromo-2-butanone (1.7 ml; 15.2 mmol) and K2CO3 (2.1 g; 15.2 mmol) at 30° C. for 24 h. After aqueous work-up and purification by RP chromatography the pure material (0.65 g) is de-acetylated in MeOH (70 ml) using DBU (0.6 ml) at reflux. After aqueous work-up 5-amino-3,3-dimethyl-6-nitro-1-(2-oxo-butyl)-1,3-dihydro-indol-2-one (0.57 g) is obtained and used without further purification.

Workup

  1. customat 30° C.
  2. customfor 24 h
  3. customAfter aqueous work-up and purification by RP chromatography the pure material (0.65 g)
  4. temperatureat reflux

Sources & evidence

ORD record
ord-c9bb9df487514f4aae7eaa47a183e6b8
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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