Butyl iodide → 5-Amino-1-butyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one

HRID 2235336Notes

Reaction equation

HRID 2235336 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](I)[CH2:21][CH2:22][CH3:23].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl.CO>CC(O)C.Cl>[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][CH2:21][CH2:22][CH3:23])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

7

Reactant 4

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 178027335-Amino-1-butyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-oneYield 60.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

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 butyl iodide (1.8 ml; 15.4 mmol) and K2CO3 (2.1 g; 15.2 mmol) at RT for 20 h. After aqueous work-up and flash chromatography on silica gel eluting with CH2Cl2/MeOH (30:1) the alkylated acetamide (0.94 g; 2.93 mmol) is de-acetylated under reflux conditions in 2-propanol (3 ml) and hydrochloric acid (6 N; 11 ml). Pure 5-amino-1-butyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (0.64 g) is obtained by flash chromatography on silica gel eluted with CH2Cl2/MeOH (50:1).

Workup

  1. customat RT
  2. customfor 20 h

Sources & evidence

ORD record
ord-b733704f5e2a41b49304d9b37528846a
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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