Acetic Acid → Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate

HRID 1982416ノート

反応式

HRID 1982416 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[N:12]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[O-].[Na+].C(O)(=O)C>CO>[CH3:23][O:22][C:20]([C:19]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[C:4]([C:3]=1[OH:2])=[CH:9][C:8]([O:10][CH3:11])=[CH:7][CH:6]=2)=[O:21]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 13220377HCID 13220377、化合物

生成物 1

HCID 54696100Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate収率 82%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
20 °C

実験手順

A mixture of 1.7 kg (5.2 mole) of 5-methoxy-2-[(2-methoxy-2-oxoethyl)phenylamino]benzoic acid methyl ester, and 303 g (5.6 mole) of sodium methoxide in 10.0 l of anhydrous methanol was stirred at reflux for 90 minutes. The mixture was cooled to 20° C., filtered, and treated with 336 g (320 ml, 5.6 mole) of glacial acetic acid. The mixture was cooled in ice, and the precipitated crude product was filtered and washed with cold methanol followed by hexane. There was obtained 1267 g (82% yield) of the indole product of analytical purity, mp 114°-116° C.

後処理

  1. temperatureat reflux for 90 minutes
  2. filtrationfiltered
  3. temperatureThe mixture was cooled in ice
  4. customthe precipitated crude product
  5. filtrationwas filtered
  6. washwashed with cold methanol

出典と根拠

ORDレコード
ord-7da37bf95621464dbb8f079410dddfe1
出典データセット
uspto-grants-1986_06
特許番号
US04596814

反応ノート

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