Pyridine → 4-fluoro-N-(4-nitrophenyl)benzamide

HRID 843885Notes

Reaction equation

[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>ClCCl.FC1C=CC(C(Cl)=O)=CC=1.N1C=CC=CC=1>[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:23])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 30.0 gm (0.217 mole) 4-nitroaniline in 225 mL dichloromethane were added 17.57 mL (0.217 mole) pyridine. The suspension was cooled to 0° C. and then 25.66 mL (0.217 mole) 4-fluorobenzoyl chloride were added slowly. Within 15 minutes the reaction mixture became homogeneous and was allowed to warm to room temperature. After an hour an additional 2.56 mL (21.7 mMol) 4-fluorobenzoyl chloride and 1.75 mL (21.7 mMol) pyridine were added and the reaction continued at room temperature for an additional hour. The reaction mixture was then washed with 200 mL water at which point a precipitate formed. The solid was filtered, washed with 100 mL hexane, washed with 200 mL water and dried under reduced pressure at 60° C. to give 56.6 gm (100%) of the desired compound.

Workup

temperatureto warm to room temperature
waitthe reaction continued at room temperature for an additional hour
washThe reaction mixture was then washed with 200 mL water at which point a precipitate
customformed
filtrationThe solid was filtered
washwashed with 100 mL hexane
washwashed with 200 mL water
customdried under reduced pressure at 60° C.

Sources & evidence

ORD record: ord-d2e25913b5d74067938b27c02cf3716e
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380201B1

Reaction notes

Loading…