Acetonitrile → 5-Amino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-one

HRID 2235340Notes

Reaction equation

HRID 2235340 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][CH2:23][CH3:24].C([O-])([O-])=O.[K+].[K+].CC#N>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][CH2:23][CH3:24])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 123351-IodopentaneHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 178027445-Amino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-oneYield 73.6%

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 (50 g) is alkylated using pentyliodide (76.8 g; 0.38 mol) and K2CO3 (53.6 g; 0.38 mol) at 60° C. for 24 h. After aqueous work-up the crude material is de-acetylated under reflux in 2-propanol (500 ml) and hydrochloric acid (6 N; 300 ml). After aqueous work-up pure 5-amino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-one (40.7 g) is obtained by re-crystallization from MeCN.

Workup

  1. customat 60° C.
  2. customfor 24 h

Sources & evidence

ORD record
ord-23875b24c5ab43c18526af3c20313877
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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