4-Bromobutyryl chloride → HCID 66620617, compound

HRID 415505Notes

Reaction equation

HRID 415505 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH2:12].[Br:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18]>ClCCCl.ClCCl>[Br:13][CH2:14][CH2:15][CH2:16][C:17]([NH:12][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[Cl:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:18]

Participants

5

Reactant 2

HCID 702254-Bromobutyryl chlorideHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 66620617HCID 66620617, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloroquinolin-3-amine (3.70 g, 20.74 mmol) and 4-bromobutyryl chloride (11.54 g, 62.22 mmol) dissolved in 100 mL of 1,2-dichloroethane was heated to reflux. After 17 hours the reaction was cooled to room temperature, diluted with dichloromethane, washed with saturated aqueous K2CO3, H2O and brine, dried over Na2SO4, and concentrated under reduced pressure to give a brown solid. The solid was triturated with a mixture of hexane and ether, filtered and dried to give 4-bromo-N-(4-chloroquinolin-3-yl)butanamide (3.65 g) as a brown solid.

Workup

  1. temperaturewas heated to reflux
  2. washwashed with saturated aqueous K2CO3, H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a brown solid
  6. customThe solid was triturated with a mixture of hexane and ether
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-381d956fffe049c08628c1c6ebe05d7e
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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