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

HRID 1982416노트

반응식

HRID 1982416 반응식
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]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 13220377HCID 13220377, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7da37bf95621464dbb8f079410dddfe1
출처 데이터셋
uspto-grants-1986_06
특허 번호
US04596814

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