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

HRID 1902823

Reaction equation

HRID 1902823 reaction equation
[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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 113598-AminoquinolineHCID 783704-Chlorobutyryl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-ddf634dbbf72471799d7274361139b10
Source dataset
uspto-grants-1982_12
Patent number
US04366158

Linked notes

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