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

HRID 8123

反応式

HRID 8123 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4866853a2f2646d1ab550d48cec29d92
出典データセット
uspto-grants-2006_08
特許番号
US07087635B2

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