Triethylamine → 4-chloro-N-(8-quinolyl)butyramide

HRID 1902823

반응식

HRID 1902823 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(N(CC)CC)C.[Cl:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>O1CCCC1>[Cl:19][CH2:20][CH2:21][CH2:22][C:23]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)=[O:24]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 113598-AminoquinolineHCID 783704-Chlorobutyryl chloride

생성물 1

HCID 128985464-chloro-N-(8-quinolyl)butyramide수율 53%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 8-aminoquinoline (10 L g, 0.069 mole) and triethylamine (10 ml, 0.072 mole) in dry tetrahydrofuran (40 ml) was treated dropwise at room temperature with 4-chlorobutyryl chloride (about 0.07 mole) until the green reaction mixture turned yellow in colour. The reaction was filtered and the solids (triethylamine hydrochloride) were washed with tetrahydrofuran. The combined filtrates were concentrated by vacuum distillation, (≃15 mm Hg), filtered over alumina in methylene chloride, concentrated and recyrstallized from ether/petroleum ether affording 4-chloro-N-(8-quinolyl)butyramide. An analytical sample was prepared by recrystallization (m.p. 62°-63°), yield 53%.

후처리

  1. filtrationThe reaction was filtered
  2. washthe solids (triethylamine hydrochloride) were washed with tetrahydrofuran
  3. concentrationThe combined filtrates were concentrated by vacuum distillation, (≃15 mm Hg),
  4. filtrationfiltered over alumina in methylene chloride
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ddf634dbbf72471799d7274361139b10
출처 데이터셋
uspto-grants-1982_12
특허 번호
US04366158

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