Hydrochloric Acid → 4-(Pyridin-4-yl)benzoic acid hydrochloride

HRID 1192416Notes

Reaction equation

HRID 1192416 reaction equation
C([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)C.[ClH:18]>O>[ClH:18].[N:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:17])=[O:3])=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15294733Ethyl 4-(pyridin-4-yl)benzoate

Product 1

HCID 574326074-(Pyridin-4-yl)benzoic acid hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 4-pyridin-4-yl-benzoic acid ethyl ester (430 mg, 1.89 mmol) was heated to 100° C. in 6.5 mL of 3M HCl solution overnight to completion. The mixture was cooled to room temperature and diluted with water (dissolves precipitate). The solution was filtered and concentrated in vacuo to afford the 4-pyridin-4-yl-benzoic acid hydrochloride salt as a pale yellow solid (380 mg, 85%). 1H NMR (DMSO-d6, 400 MHz) δ 8.93 (d, J=5.6 Hz, 2H), 8.27 (d, J=5.6 Hz, 2H), 8.13 (d, J=8.0 Hz, 2H), 8.09 (d, J=8.0 Hz, 2H), —CO2H or —NH+ not observed. LCMS (APCI+) m/z 200 [M+H]+; Rt=1.05 min.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74c40bcea6cc41c7b6470daa7ce8a072
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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