Isopropyl iodide → HCID 17802746, compound

HRID 2235354Notes

Reaction equation

HRID 2235354 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].[CH:20](I)([CH3:22])[CH3:21].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]([CH:20]([CH3:22])[CH3:21])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 17802746HCID 17802746, compoundYield 30%

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 isopropyl iodide (1.6 ml; 15.5 mmol) and K2CO3 (2.1 g; 15.2 mmol) at RT for 7 days. After aqueous work-up and flash chromatography on silica gel eluting with CH2Cl2/MeOH (30:1) the pure alkylated acetamide (0.45 g; 1.46 mmol) is de-acetylated under reflux in 2-propanol (1.5 ml) and hydrochloric acid (6 N; 5.5 ml). After completion of the reaction the mixture is poured into ice-water and the precipitate is collected to give pure 5-amino-1-isopropyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (0.3 g).

Workup

  1. customat RT
  2. customfor 7 days
  3. customAfter completion of the reaction the mixture
  4. customthe precipitate is collected

Sources & evidence

ORD record
ord-01a7e32a44394d1084167aee768bf911
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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