Acetyl chloride → HCID 67506066, compound

HRID 2105494Notes

Reaction equation

HRID 2105494 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[Cl:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[NH:1][C:20](=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 67506066HCID 67506066, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-amino-4-chloroquinoline (20.0 g, 112 mmol) in dichloromethane (125 mL) was cooled to 0° C. Triethylamine (47.0 mL, 0.336 mol) was added followed by a solution of acetyl chloride (16.0 mL, 0.224 mol) in dichloromethane (45 mL), which was added dropwise. The reaction was stirred overnight at room temperature. An analysis by LC/MS indicated the presence of starting material, and additional acetyl chloride (4 mL, 56 mmol) was added. The reaction was stirred for four hours at room temperature. Saturated aqueous sodium bicarbonate (100 mL) was added, and the mixture was stirred for three days. The organic layer was separated and washed with saturated aqueous sodium bicarbonate (2×50 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide N-(4-chloroquinolin-3-yl)acetamide as a dark red solid.

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. stirringThe reaction was stirred for four hours at room temperature
  4. stirringthe mixture was stirred for three days
  5. customThe organic layer was separated
  6. washwashed with saturated aqueous sodium bicarbonate (2×50 mL)
  7. dry with materialdried over potassium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4dcb23e2b725425eb248656aef2c9bfc
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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