Water → 2-(6-Bromopyridin-3-ylamino)-5-chlorobenzoic acid

HRID 42043

Reaction equation

HRID 42043 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C([O-])([O-])=O.[K+].[K+].O>COCCOC>[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:10]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 57842,5-Dichlorobenzoic acidHCID 11430Potassium CarbonateHCID 6428116-Bromopyridin-3-amine

Product 1

HCID 866572592-(6-Bromopyridin-3-ylamino)-5-chlorobenzoic acidYield 34.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6-bromopyridin-3-amine (27.27 mmol, 4.70 g), 2,5-dichlorobenzoic acid (54.34 mmol, 10.38 g), Cu (2.71 mmol, 0.2 g), Cu2O (1.36 mmol, 0.2 g) and K2CO3 (54.27 mmol, 7.5 g) in 1,2-dimethoxiethane (40 ml) was heated in a microwave oven at 130° C. for 14 hours, under nitrogen atmosphere. Water was added and the mixture was filtered through celite and extracted with AcOEt. The organic phase was washed with saturated K2CO3 aqueous solution and brine. The solvent was evaporated to afford 3.08 g (yield 31%) of the expected product.

Workup

  1. filtrationthe mixture was filtered through celite
  2. extractionextracted with AcOEt
  3. washThe organic phase was washed with saturated K2CO3 aqueous solution and brine
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5fc2bee7eea0409d8f13fead24c1c4c6
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Linked notes

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