Acetyl chloride → Acetyl chloride

HRID 415527Notes

Reaction equation

HRID 415527 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27]([Cl:30])(=[O:29])[CH3:28]>ClCCl>[C:27]([Cl:30])(=[O:29])[CH3:28].[C:27]([O:19][CH2:18][CH2:17][CH2:16][NH:15][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 6367Acetyl chloride3×HCID 8471TriethylamineHCID 666198783-[(7-Bromo-3-nitroquinolin-4-yl)amino]propan-1-ol

Product 2

HCID 6367Acetyl chlorideHCID 666202383-[(7-Bromo-3-nitroquinolin-4-yl)amino]propyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a round-bottomed flask containing 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol (88.15 g) was added dichloromethane (DCM, 600 mL) followed by triethylamine (38 mL, 270.8 mmol) and the solution was stirred for 5 minutes. In a separate flask a solution of acetyl chloride (14.4 mL, 202.5 mmol) in dichloromethane (300 mL) was prepared. The acetyl chloride solution was added to the reaction mixture in a dropwise fashion. The reaction was stirred at ambient temperature for 4 h. Additional acetyl chloride (2.8 mL in DCM (50 mL)) was added and the reaction mixture was stirred at ambient temperature overnight. At this time additional acetyl chloride (1.4 mL in dichloromethane (25 mL)) was added and the reaction was stirred at ambient temperature for 1 h. Additional dichloromethane (200 mL) was then added and the reaction was transferred to a separatory funnel. The organic layer was washed with water (2×800 mL) and brine (1×800 mL). The organic layer was separated, dried (MgSO4), filtered, and the solvent evaporated to afford 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propyl acetate (60.8 g) as a bright yellow solid.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 4 h
  2. stirringthe reaction mixture was stirred at ambient temperature overnight
  3. stirringthe reaction was stirred at ambient temperature for 1 h
  4. customthe reaction was transferred to a separatory funnel
  5. washThe organic layer was washed with water (2×800 mL) and brine (1×800 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-8e9d61e39dd84c6fb066ab357be9b79a
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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