Hydrochloric Acid → N-(2-Fluorophenyl) cinnamamide

HRID 2035640Notes

Reaction equation

HRID 2035640 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-60a9ba35cc9344f7928ae51ec43d6931
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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