Dimethylformamide → HCID 18508338, compound

HRID 1356444Notes

Reaction equation

HRID 1356444 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[C:12]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][C:15]([CH2:18]Br)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[C:12]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=[CH:14][C:15]([CH2:18][N:3]2[C:2](=[O:1])[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 178498304HCID 178498304, compound

Product 1

HCID 18508338HCID 18508338, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 6-hydroxynicotinate (3 g), 4-biphenylylmethyl bromide (5.8 g), potassium carbonate (8.2 g), and DMF (30 ml) was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride sequentially and concentrated. The resulting crystals were washed with diisopropylether and recrystallized from ethyl acetate/hexane to obtain the titled compound (5.1 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride sequentially
  3. concentrationconcentrated
  4. washThe resulting crystals were washed with diisopropylether
  5. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-eecc3e774c084a648f893a8a6db00bc3
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

Loading…