Ammonium Hydroxide → 6-Bromo-4-chloro-3-quinolinecarboxamide

HRID 1486923Notes

Reaction equation

HRID 1486923 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](Cl)=[O:13])=[C:5]2[Cl:15].[OH-].[NH4+:17]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([NH2:17])=[O:13])=[C:5]2[Cl:15]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 1184987196-Bromo-4-chloro-3-quinolinecarbonyl chloride

Product 1

HCID 675142646-Bromo-4-chloro-3-quinolinecarboxamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DMF (1.506 mL, 19.37 mmol) was added to 6-bromo-4-oxo-1H-quinoline-3-carboxylic acid (51.93 g, 193.72 mmol) and thionyl chloride (353 mL, 4843.07 mmol) at r.t. and the resulting solution stirred at 70° C. for 2 h under an inert atmosphere. The resulting solution was evaporated to dryness and the residue azeotroped with toluene to afford 6-bromo-4-chloroquinoline-3-carbonyl chloride (62.13 g). The 6-bromo-4-chloroquinoline-3-carbonyl chloride was dissolved in DCM (420 mL) and added portionwise to ammonium hydroxide (251 mL, 1937.23 mmol) at 0° C. over 15 minutes. The organic solvent was removed under reduced pressure and the solid collected by filtration, washed with water, Et2O and then dried to afford the desired material (52.8 g, 95%) as a white solid. NMR Spectrum: 1H NMR (500 MHz, DMSO-d6) δ 8.00-8.11 (3H, m), 8.24 (1H, s), 8.45 (1H, s), 8.92 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=287.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. filtrationthe solid collected by filtration
  3. washwashed with water, Et2O
  4. customdried

Sources & evidence

ORD record
ord-4b86636011a3436da46ac5c91c64661e
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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