Pyridine → N-(3-Chlorophenyl)-2-methyl-3-phenylacrylamide

HRID 1432846Notes

Reaction equation

HRID 1432846 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].N1C=CC=CC=1.[CH3:15][C:16](=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17](Cl)=[O:18]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:17](=[O:18])[C:16]([CH3:15])=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 79323-ChloroanilineHCID 230201alpha-Methylcinnamoylchloride

Product 1

HCID 3497717N-(3-Chlorophenyl)-2-methyl-3-phenylacrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-chloroaniline (0.98 mL, 9.3 mmol) in CH2Cl2 (25 mL) at 0° C. is added pyridine (0.78 mL, 9.5 mmol). To the resulting solution is added dropwise a solution of α-methyl cinnamic acid chloride (1.6 g, 9.3 mmol) in CH2Cl2 (8 mL). After 3 hours, the solution is concentrated. The crude product is purified by column chromatography eluting with 5% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound is obtained as a solid (2.5 g, 9.2 mmol). 1H NMR (CDCl3, 300 MHz) δ7.95 (m, 1H), 7.73 (s, 1H), 7.46 (m, 1H), 7.33 (m, 6H), 7.22 (m, 1H), 7.03 (m, 1H), 2.13 (s, 3H).

Workup

  1. concentrationthe solution is concentrated
  2. customThe crude product is purified by column chromatography
  3. washeluting with 5% EtOAc/hexanes to 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-d75b3cf4cbe34783ac2c494fa33f0625
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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