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

HRID 8123

반응식

HRID 8123 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4866853a2f2646d1ab550d48cec29d92
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087635B2

연결된 노트

불러오는 중…