Pyridine → HCID 532828, compound

HRID 271829Notes

Reaction equation

HRID 271829 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].N1C=CC=CC=1.[C:15]1([CH2:21][CH2:22][C:23](Cl)=[O:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:23](=[O:24])[CH2:22][CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 79323-ChloroanilineHCID 64801Benzenepropanoyl chloride

Product 1

HCID 532828HCID 532828, compoundYield 106.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-chloroaniline (8.3 ml, 78.4 mmol), DMAP (1.0 g, 7.8 mmol), and pyridine (6.9 ml, 86.2 mmol) in anhydrous DCM (150 ml) at 0° C., was added 3-phenylpropionyl chloride (12.8 ml, 86.2 mmol). The mixture was warmed to ambient temperature and stirred under N2 overnight. Excess DCM was added to the reaction mixture. The organic layer was washed with 1N HCl (3×), saturated NaHCO3 (3×), brine, dried over MgSO4, and the solvent was removed in vacuo to yield 21.6 g of N-(3-chlorophenyl)-3-phenylpropanamide 21 as a peach colored crude solid.

Workup

  1. washThe organic layer was washed with 1N HCl (3×), saturated NaHCO3 (3×), brine
  2. dry with materialdried over MgSO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5724c2fb246b41d7b1660379414e016e
Source dataset
uspto-grants-2008_11
Patent number
US07452996B2

Reaction notes

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