Phosphorus oxychloride → ethyl 5-chloro-3-formyl-1H-indole-2-carboxylate

HRID 2104397노트

반응식

HRID 2104397 반응식
P(Cl)(Cl)(Cl)=O.CN([CH:14]=[O:15])C1C=CC=CC=1.[CH2:16]([O:18][C:19]([C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[O:20])[CH3:17].C([O-])(=O)C.[Na+]>ClCCCl>[CH2:16]([O:18][C:19]([C:21]1[NH:22][C:23]2[C:28]([C:29]=1[CH:14]=[O:15])=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[O:20])[CH3:17]

참가 물질

6

반응물 4

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 517045Sodium Acetate

생성물 1

HCID 4410568ethyl 5-chloro-3-formyl-1H-indole-2-carboxylate수율 79.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

Phosphorus oxychloride (2.0 mL) was added to N-methylformanilide (2.9 g), and after the mixture was stirred for 15 minutes, 1,2-dichloroethane (50 mL) and 5-chloroindole-2-carboxylic acid ethyl ester (4.0 g) were added thereto, followed by heating under reflux for 1 hour. The reaction mixture was poured into an aqueous solution (28 mL) of sodium acetate (14 g) under ice cooling, and the thus-obtained mixture was stirred for 18 hours. Insoluble matter was collected by filtration, and was sequentially washed with water and diethyl ether, to thereby give the title compound (3.56 g).

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. stirringthe thus-obtained mixture was stirred for 18 hours
  4. filtrationInsoluble matter was collected by filtration
  5. washwas sequentially washed with water and diethyl ether

출처 및 근거

ORD 기록
ord-1ab6c9c7a64a4bd69c583c9c181a6c61
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576135B2

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