2-Fluoroaniline → N-(2-Fluorophenyl) cinnamamide

HRID 1019783Notes

Reaction equation

HRID 1019783 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[C:15](Cl)(=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.CC(C)=O>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:15](=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 95842-FluoroanilineHCID 11430Potassium CarbonateHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 303250N-(2-Fluorophenyl) cinnamamideYield 103.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-fluoroaniline (25.0 g, 225 mmol) and potassium carbonate (47 g, 337 mmol) in water (112 mL) and acetone (45 mL) at 0° C. was added cinnamoyl chloride (37.0 g, 225 mmol, 1 eq) in acetone (45 mL) over 2 h. The reaction was stirred for 1 h at 0° C., and quenched into 200 mL of ice-water. The white crystalline solid was filtered and washed with water. The solid was air dried for 2 h, then washed with 400 mL of hexanes. The solid was dried under vacuum overnight to afford N-(2-fluorophenyl)cinnamamide (56 g, 103% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.49 (br t, J=7.8 Hz, 1H), 7.80 (d, J=15.3 Hz, 1H), 7.57 (m, 3H), 7.41 (m, 3H), 7.17 (m, 3H), 6.61 (d, J=15.6 Hz, 1H). Mass Spectrum (ESI) m/e=242.1 (M+1).

Workup

  1. customquenched into 200 mL of ice-water
  2. filtrationThe white crystalline solid was filtered
  3. washwashed with water
  4. customdried for 2 h
  5. washwashed with 400 mL of hexanes
  6. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-63518db6d3f44171bbac0f372ffad46d
Source dataset
uspto-grants-2014_05
Patent number
US08716290B2

Reaction notes

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