Triethylamine → HCID 57447109, compound

HRID 2105462Notes

Reaction equation

HRID 2105462 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[NH2:14][C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:24]=1[Cl:25])=[CH:22][CH:21]=[CH:20][CH:19]=2>ClCCl>[Cl:25][C:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[NH:14][C:1](=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 57447109HCID 57447109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Butyryl chloride (3.77 mL, 1.3 eq) and triethylamine (5.85 mL, 1.3 eq) were added sequentially to a chilled (0° C.) solution of 3-amino-4-chloroquinoline (5.0 g, 1.0 eq) in dichloromethane (100 mL). The reaction mixture was warmed to ambient temperature and then allowed to stir overnight. The reaction mixture was quenched with aqueous saturated sodium bicarbonate. The organic layer was separated and concentrated under reduced pressure to provide 6.5 g of N-(4-chloroquinolin-3-yl)butyramide.

Workup

  1. customThe reaction mixture was quenched with aqueous saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e9f40f6bb0c408e8d1e99dead1287cb
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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