Hydrochloric Acid → 5-(4-Cyclopropyl-1H-imidazol-1-yl)-2-fluoro-4-methylbenzoic acid hydrochloride
Reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[C:10]([CH3:18])=[CH:11][C:12]([F:17])=C([CH:16]=3)C#N)[CH:8]=2)[CH2:3][CH2:2]1.[CH3:19][C:20](=[O:24])[O:21]CC.[ClH:25]>>[ClH:25].[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[C:10]([CH3:18])=[CH:11][C:12]([F:17])=[C:19]([CH:16]=3)[C:20]([OH:21])=[O:24])[CH:8]=2)[CH2:3][CH2:2]1Participants
Conditions
- Temperature
- 100 °C
Procedure
5-(4-Cyclopropyl-1H-imidazol-1-yl)-2-fluoro-4-methylbenzonitrile (11.21 g, 46.50 mmol) was placed in a round bottom flask fitted with a reflux condenser, and suspended in 38% hydrochloric acid (200 mL). The mixture was heated to 100° C. for 4.5 hours, and then cooled to room temperature. Solvent was removed under reduced pressure to give a pink solid, to which was added 100 ml of EA. The solid product was collected by filtration and washed with 3×100 mL EA. To the solid product was added 100 mL 10% methanol in dichloromethane, the mixture stirred, and the filtrate collected. This was repeated with 2 more 100 ml portions of 10% methanol in dichloromethane. The filtrates were combined and solvent was removed under reduced pressure, to provide crude 5-(4-cyclopropyl-1H-imidazol-1-yl)-2-fluoro-4-methylbenzoic acid hydrochloride. No further purification was carried out (11.13 g, 37.54 mmol). Anal. LC/MS (m/z: 261, M+1)
Workup
- customfitted with a reflux condenser
- temperaturecooled to room temperature
- customSolvent was removed under reduced pressure
- customto give a pink solid
- filtrationThe solid product was collected by filtration
- washwashed with 3×100 mL EA
- additionTo the solid product was added 100 mL 10% methanol in dichloromethane
- customthe filtrate collected
- customsolvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-d883a97e70144b10ba6b23b6fa10b982
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09333197B2
Reaction notes
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