2-Nitropropane → HCID 22038580, compound

HRID 914944Notes

Reaction equation

HRID 914944 reaction equation
I.CN([CH2:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)C.CI.C[O-].[Na+].[N+:20]([CH:23]([CH3:25])[CH3:24])([O-:22])=[O:21]>CO.C(OCC)(=O)C.[NH4+].[Cl-]>[CH3:24][C:23]([N+:20]([O-:22])=[O:21])([CH3:25])[CH2:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1

Participants

8

Reactant 4

HCID 3982-NitropropaneHCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 22038579HCID 22038579, compound

Product 1

HCID 22038580HCID 22038580, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A 0° C. solution of 3-dimethylaminomethyl-1H-7-azaindole hydroiodide (10 g, 33 mmol) in 46 ml of methanol and 46 ml of 2-nitropropane is treated with methyl iodide (2.15 ml, 35 mmol) and solid sodium methoxide (3.65 g, 68 mmol) sequentially. The resulting mixture is allowed to warm to ambient temperature, and, after stirring overnight, the reaction mixture is diluted with ethyl acetate (100 ml) and saturated aqueous NH4Cl solution (100 ml). The aqueous layer is extracted with ethyl acetate (2×100 ml), and the combined organic layers are dried over Na2SO4 and concentrated in vacuo to give 3-(2-methyl-2-nitropropyl)-1H-7-azaindole in 92% yield.

Workup

  1. extractionThe aqueous layer is extracted with ethyl acetate (2×100 ml)
  2. dry with materialthe combined organic layers are dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf1e53cbdc9f4390a7030884cf8ba856
Source dataset
uspto-grants-2007_09
Patent number
US07265127B2

Reaction notes

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