Iodoethane → 5-Amino-1-ethyl-3,3-dimethyl-6-nitro-1.3-dihydro-indol-2-one

HRID 2235335Notes

Reaction equation

HRID 2235335 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)[CH3:21].C([O-])([O-])=O.[K+].[K+]>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][CH3:21])[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 230926495-Amino-1-ethyl-3,3-dimethyl-6-nitro-1.3-dihydro-indol-2-one

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 (0.75 g) is alkylated using ethyl iodide (0.5 ml; 5.7 mmol) and K2CO3 (1.6 g; 11.6 mmol) at 55° C. for 7 h. After aqueous work-up the crude alkylated acetamide (0.8 g; 2.74 mmol) is de-acetylated under reflux conditions in 2-propanol (3 ml) and hydrochloric acid (5 ml). After aqueous work-up the crude 5-amino-1-ethyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (0.6 g) is used without further purification.

Workup

  1. customat 55° C.
  2. customfor 7 h
  3. customAfter aqueous work-up the crude 5-amino-1-ethyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (0.6 g) is used without further purification

Sources & evidence

ORD record
ord-b6003fe6977a42388b981660d7010a7a
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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