Benzyl Bromide → 5-Amino-1-benzyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one

HRID 2235346Notes

Reaction equation

HRID 2235346 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].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.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]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 230926775-Amino-1-benzyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1 g) is alkylated using benzyl bromide (0.46 ml; 3.9 mmol) and K2CO3 (1.5 g; 10.9 mmol) at RT for 20 h. After filtration and evaporation of the solvent the crude material is de-acetylated under reflux conditions in 2-propanol (10 ml) and hydrochloric acid (6 N, 30 ml). Pure 5-amino-1-benzyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (1.04 g) precipitates by pouring the reaction mixture into ice-water.

Workup

  1. customat RT
  2. customfor 20 h
  3. filtrationAfter filtration and evaporation of the solvent the crude material
  4. customPure 5-amino-1-benzyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (1.04 g) precipitates
  5. additionby pouring the reaction mixture into ice-water

Sources & evidence

ORD record
ord-9c9666f21e10417aa2e317e01a7f2ba2
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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