Diethyl Ether → 6-(2'-Chlorocinnamoyl)amino-4-methoxy-2-methyl-quinoline

HRID 580811노트

반응식

HRID 580811 반응식
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6](Cl)=[O:7].[NH2:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[C:19]([CH3:24])[CH:18]=[C:17]2[O:25][CH3:26].CCOCC>C(O)(=O)C>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([NH:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[C:19]([CH3:24])[CH:18]=[C:17]2[O:25][CH3:26])=[O:7]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 2737382HCID 2737382, 화합물HCID 151333914-Methoxy-2-methylquinolin-6-amine

생성물 1

HCID 536780766-(2'-Chlorocinnamoyl)amino-4-methoxy-2-methyl-quinoline

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

A solution of 2-chlorocinnamoyl chloride (prepared by treatment of 2-chlorocinnamic acid with oxalyl cloride and catalytic DMF in dichloromethane) (0.27 gm) in 1 mL acetic acid was added to a solution of 6-amino-4-methoxy-2-methyl-quinoline (0.25 g, 1.33 mmol) in glacial acetic acid (3 mL). A heavy precipitate formed, and the mixture was stirred for 1 h at room temperature. Ether (25 mL) was added and the solid was filtered, washed with ether, and dried by suction. The hydrochloride salt was suspended in warm water (25 mL) and ethanol (25 mL) and heated until dissolved. After cooling to room temperature, 5N sodium hydroxide was added to give a white precipitate that was filtered, and washed with water. Recrystallization from ethanol afforded the title compound; yield 0.27 g (58%); m.p. 228-229°; MS (FAB): m/z 353 (M+1).

후처리

  1. customA heavy precipitate formed
  2. filtrationthe solid was filtered
  3. washwashed with ether
  4. customdried by suction
  5. temperatureethanol (25 mL) and heated
  6. dissolutionuntil dissolved
  7. temperatureAfter cooling to room temperature
  8. addition5N sodium hydroxide was added
  9. customto give a white precipitate that
  10. filtrationwas filtered
  11. washwashed with water
  12. customRecrystallization from ethanol

출처 및 근거

ORD 기록
ord-f3bd4a11a0aa45219b08e67d8159804e
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919776

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