3-Chloropropionyl chloride → HCID 66619827, compound

HRID 415514Notes

Reaction equation

HRID 415514 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].[Cl:13][CH2:14][CH2:15][C:16](Cl)=[O:17]>ClCCCl.ClCCl>[Cl:13][CH2:14][CH2:15][C:16]([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:17]

Participants

5

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 8173324-chloroquinolin-3-amine

Product 1

HCID 66619827HCID 66619827, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-chloroquinolin-3-amine (6.00 g, 33.59 mmol) and 3-chloropropionyl chloride (4.8 mL, 50.39 mmol) dissolved in 200 mL of 1,2-dichloroethane was heated to 50° C. in an oil bath. After 20 hrs the temperature of the oil bath was increased to 90° C. After an additional 26 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 7.12 g of 3-chloro-N-(4-chloroquinolin-3-yl)propanamide as a tan solid.

Workup

  1. temperatureAfter 20 hrs the temperature of the oil bath was increased to 90° C
  2. temperatureAfter an additional 26 hours the reaction was cooled to room temperature
  3. washwashed with saturated aqueous K2CO3, H2O, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfa8a7e0902b43f7b8d681a409315afe
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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