2-Nitropropane → 3-(2-methyl-2-nitropropyl)-1H-indole-4-carboxylic acid methyl ester

HRID 8123

Reaction equation

HRID 8123 reaction equation
I.[CH3:2][O:3][C:4]([C:6]1[C:7]2[C:8]([CH2:15]N(C)C)=[CH:9][NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:5].S(OC)(OC)(=O)=O.C[O-].[Na+].[N+:29]([CH:32]([CH3:34])[CH3:33])([O-:31])=[O:30]>CO.C(OCC)(=O)C.[NH4+].[Cl-]>[CH3:2][O:3][C:4]([C:6]1[C:7]2[C:8]([CH2:15][C:32]([CH3:34])([N+:29]([O-:31])=[O:30])[CH3:33])=[CH:9][NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:5]

Participants

8

Reactant 4

HCID 3982-NitropropaneHCID 6497Dimethyl SulfateHCID 10942334Sodium MethoxideHCID 695180113-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide

Product 1

HCID 695180953-(2-methyl-2-nitropropyl)-1H-indole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A 0° C. solution of 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide (19 g, 52.7 mmol) in 75 ml of methanol and 75 ml of 2-nitropropane is treated with dimethyl sulfate (10 ml, 105.5 mmol) and solid sodium methoxide (6.3 g, 110.6.mmol) sequentially. The resulting mixture is allowed to warm to ambient temperature, and, after stirring overnight, the reaction mixture is diluted with ethyl acetate (300 ml) and saturated aqueous NH4Cl solution (500 ml). The aqueous layer is extracted with ethyl acetate (200 ml), and the combined organic layers are dried over Na2SO4 and concentrated in vacuo to give 3-(2-methyl-2-nitropropyl)-1H-indole-4-carboxylic acid methyl ester in quantitative yield.

Workup

  1. extractionThe aqueous layer is extracted with ethyl acetate (200 ml)
  2. dry with materialthe combined organic layers are dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4866853a2f2646d1ab550d48cec29d92
Source dataset
uspto-grants-2006_08
Patent number
US07087635B2

Linked notes

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