Hydrochloric Acid → N-(2-Fluorophenyl) cinnamamide

HRID 876477Notes

Reaction equation

HRID 876477 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].N1C=CC=CC=1.Cl>C1COCC1>[F:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH:15][C:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 95842-FluoroanilineHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 303250N-(2-Fluorophenyl) cinnamamideYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Cinnamoyl chloride (89.2 g, 535 mmol) was dissolved in THF (170 mL) and added dropwise to a 0° C. solution of 2-fluoroaniline (54.1 g, 486 mmol) and pyridine (39.35 mL, 486.5 mmol) dissolved in THF (170 mL). The mixture was allowed to warm to ambient temperature after the addition and stirred for 15 hours. A solution of 2M HCl was added (1250 mL) and the mixture was stirred at ambient temperature for 8 hours, during which the initial oil solidified to a light pink solid. This material was collected by filtration, washed with several portions of water, and air-dried to provide the desired product (119.5 g).

Workup

  1. additionafter the addition
  2. stirringthe mixture was stirred at ambient temperature for 8 hours, during which the initial oil
  3. filtrationThis material was collected by filtration
  4. washwashed with several portions of water
  5. customair-dried

Sources & evidence

ORD record
ord-e420f71d5d044733beb6ebca854090f9
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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