Hydrochloric Acid → Acetamide, N-3-quinolinyl-

HRID 901941Notes

Reaction equation

HRID 901941 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[NH2:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2.Cl>ClCCl.C(Cl)(Cl)Cl>[C:1]([NH:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 113753-Aminoquinoline

Product 1

HCID 79448Acetamide, N-3-quinolinyl-Yield 85.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (410 mg, 5.2 mmol) and triethylamine (620 mg, 6.2 mmol) were added to a solution of 3-aminoquinoline (710 mg, 4.9 mmol) in dichloromethane (50 ml) and the mixture was stirred at room temperature for 18 h. Chloroform (100 ml) was added, the mixture acidified with 1N hydrochloric acid (50 ml) and the phases separated. The aqueous phase was basified with 1N sodium hydroxide solution and extracted with chloroform/IPA (85:15, 175 ml). The organic extract was washed with water, brine, dried and reduced to afford 3-acetamidoquinoline (780 mg, 84%) as a yellow solid.

Workup

  1. customthe phases separated
  2. extractionextracted with chloroform/IPA (85:15, 175 ml)
  3. extractionThe organic extract
  4. washwas washed with water, brine
  5. customdried

Sources & evidence

ORD record
ord-a9fcc565b32d4b149e481f48e2a65e85
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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