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3-(3-Benzyloxy-4-bromo-phenylamino)-but-2-enoic acid ethyl ester → 7-Benzyloxy-6-bromo-2-methyl-quinolin-4-ol

HRID 1829774
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HRID 1829774 반응식
C(O[C:4](=[O:24])[CH:5]=[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1)[CH3:7])C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH2:17]([O:16][C:11]1[CH:10]=[C:9]2[C:14]([C:4]([OH:24])=[CH:5][C:6]([CH3:7])=[N:8]2)=[CH:13][C:12]=1[Br:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
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참가 물질

3

반응물 1

HCID 694724593-(3-Benzyloxy-4-bromo-phenylamino)-but-2-enoic acid ethyl ester

생성물 1

HCID 1784287967-Benzyloxy-6-bromo-2-methyl-quinolin-4-ol수율 213.2%

시약·촉매·용매 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)용매2회

반응 조건

온도
250 °C

실험 절차

Dowtherm® A (320 mL) was heated to 250° C. then a solution of 3-(3-benzyloxy-4-bromo-phenylamino)-but-2-enoic acid ethyl ester (55.5 g, 99.5 mmol) in Dowtherm® A (120 mL) was slowly added. The reaction mixture was heated 16 min at 250° C. and ethanol was collected by distillation. The mixture was cooled down, diluted with hexanes (1.5 L) and filtered. The solid was washed with ether and dried under vacuum. 73.0 g of the title compound were obtained. Brown solid, ISP-MS: m/e=345.2 ([M+H]+).

후처리

  1. distillationethanol was collected by distillation
  2. temperatureThe mixture was cooled down
  3. additiondiluted with hexanes (1.5 L)
  4. filtrationfiltered
  5. washThe solid was washed with ether
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-8371c49e54554a8aa1c77b70259f69eb
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07064134B2

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