Methanol → HCID 67425873, compound

HRID 2235378Notes

Reaction equation

HRID 2235378 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:12](=[O:14])[CH3:13])[CH:9]=2)[NH:4][C:3]1=[O:18].CCN(CC)CC.C[C:28]1([CH3:37])N([O])[C:32](C)(C)[CH2:31][CH2:30][CH2:29]1.CO>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[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:12](=[O:14])[CH3:13])[CH:9]=2)[N:4]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:37]=2)[C:3]1=[O:18]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 2724126TempoHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 67425873HCID 67425873, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of phenyl bronic acid (0.47 g; 3.9 mmol), N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (0.5 g; 1.9 mmol) and NEt3 (0.5 μl; 3.9 mmol) in CH2Cl2 (15 ml) is added molsieves (150 mg; 4 Å), Cu(OAc)2 (70 mg; 385 μmol) and finally TEMPO (0.33 g; 2.11 mmol). The reaction mixture is stirred in an open flask at RT for 7 days. After completion MeOH (20 ml) is added and the mixture is adsorbed on silica gel. Purification by chromatography gives N-(3,3-dimethyl-6-nitro-2-oxo-1-phenyl-2,3-dihydro-1H-indol-5-yl)-acetamide (0.35 g). The material is de-acetylated in MeOH (10 ml) using DBU (80 μl) at reflux. After aqueous work-up 5-amino-3,3-dimethyl-6-nitro-1-phenyl-1,3-dihydro-indol-2-one (0.3 g) is obtained and used without further purification.

Workup

  1. customPurification by chromatography

Sources & evidence

ORD record
ord-83ee49da09864e58808c752fafee0035
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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