Potassium Carbonate → HCID 21819194, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)[CH3:2].[OH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:17]2[CH:18]=[CH:19][C:14](=[O:13])[CH:15]=[CH:16]2)=[CH:7][CH:6]=1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
In a 500 ml round bottom flask with stirbar was place 4-fluorobenzoic acid ethyl ester (16.8 g, 100 mmol), 4-hydroxypyridine (14.26 g, 150 mmol), potassium carbonate (20.7 g, 150 mmol) and N-methylpyrrolidinone (75 ml). This mixture was gradually warmed to 140° C. and kept at this temperature for three hours after which time all the starting aryl fluoride was consumed. The mixture was cooled to room temperature and with stirring ice and water was added in porions to bring the volume up to 500 ml. The precipitated product was isolated by suction filtration, washed well with water and air dried. This directly isolated material was very pure and suitable for further use. Material recrystallized from toluene had Mp 178°-180°.
Workup
- customIn a 500 ml round bottom flask with stirbar was
- customafter which time all the starting aryl fluoride was consumed
- temperatureThe mixture was cooled to room temperature and with stirring ice and water
- additionwas added in porions
- customThe precipitated product was isolated by suction filtration
- washwashed well with water and air
- customdried
- customMaterial recrystallized from toluene
Sources & evidence
- ORD record
- ord-1b42167f712a4b47bf5dcb7f3929abf4
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05783114
Reaction notes
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