Hydrochloric Acid → 2-[(2-Bromo-pyridin-4-ylmethyl)-amino]benzoic Acid

HRID 600680Notes

Reaction equation

HRID 600680 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([Br:18])[CH:13]=1.[OH-].[Na+].C(OCC)(=O)C.Cl>C(O)C>[Br:18][C:14]1[CH:13]=[C:12]([CH2:11][NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:19])=[O:2])[CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 58763671Methyl 2-{[(2-bromopyridin-4-yl)methyl]amino}benzoate

Product 1

HCID 231189932-[(2-Bromo-pyridin-4-ylmethyl)-amino]benzoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

10.0 g (31.2 mmol) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-benzoic acid methyl ester is dissolved in 290 ml of ethanol and mixed with 31.2 ml of 2 M sodium hydroxide solution. After having been stirred overnight at room temperature, the ethanol is drawn off, and the aqueous phase is shaken out with ethyl acetate. The aqueous phase is acidified with concentrated hydrochloric acid. The precipitate that is formed is suctioned off and dried. 5.93 g (62%) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-benzoic acid accumulates in the form of a white solid.

Workup

  1. customThe precipitate that is formed
  2. customdried

Sources & evidence

ORD record
ord-e111c2c5879c44039fe751a5366cf019
Source dataset
uspto-grants-2011_03
Patent number
US07902229B2

Reaction notes

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