Water → HCID 91038914, compound

HRID 1664092Notes

Reaction equation

HRID 1664092 reaction equation
Cl.[C:2]1([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.C(O[K])(C)(C)C.O>CN(C=O)C>[C:2]1([C:8]2[CH:13]=[C:12]([CH:14]=[CH:21][C:20]3[CH:23]=[CH:24][C:17]([N:16]([CH3:25])[CH3:15])=[CH:18][CH:19]=3)[CH:11]=[CH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74794-(Dimethylamino)BenzaldehydeHCID 67438976HCID 67438976, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 91038914HCID 91038914, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-phenyl-4-methylpyridine hydrochloride (1 g, 4.86 mmol) and 4-dimethylaminobenzaldehyde (0.725 g, 4.86 mmol) in anhydrous DMF (30 ml) was added solid tBuOK and the resulting mixture was stirred 5 hours at room temperature under nitrogen. Water (200 ml) was then added, the resulting yellow precipitate was filtered off and successively washed with water and Et2O to afford 650 mg (44%) of the titled compound as a yellow solid.

Workup

  1. filtrationthe resulting yellow precipitate was filtered off
  2. washsuccessively washed with water and Et2O

Sources & evidence

ORD record
ord-7dbc53b0411a4c90acbbc8900e2d2c84
Source dataset
uspto-grants-2011_10
Patent number
US08039124B2

Reaction notes

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