Sodium Chloride → 3-(2-Hydroxyethyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

HRID 2405006Notes

Reaction equation

HRID 2405006 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18](O)=[O:19])[C:12]1=[O:21].[Cl-].[Na+]>ClCCl.Cl>[OH:19][CH2:18][CH2:17][C:13]1[C:12](=[O:21])[N:11]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[CH3:1])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 56926732HCID 56926732, compound

Product 1

HCID 569267333-(2-Hydroxyethyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-oneYield 84%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

At 20° C., over the course of 20 min, 56.8 g (348 mmol) of borane-dimethylaniline complex were added dropwise to a solution of 50 g (174 mmol) of [1-(2-methyl-4-nitrophenyl)-2-oxo-1,2-dihydropyridin-3-yl]acetic acid in 100 ml of 2-methyl-THF. The mixture was after-stirred for 16 h and diluted with 500 ml of dichloromethane. Over the course of 30 min, this mixture was metered into a solution of 50 g of sodium chloride in 500 ml of 1M hydrochloric acid. The mixture was after-stirred for 1 h and the organic phase was washed again with 500 ml of a solution of 50 g of sodium chloride in 500 ml of 1M hydrochloric acid. Washing with 500 ml of a saturated aqueous sodium hydrogen carbonate solution, drying over sodium sulphate and evaporation were carried out. 40 g (84%) of the desired alcohol were obtained.

Workup

  1. customOver the course of 30 min
  2. stirringThe mixture was after-stirred for 1 h
  3. washthe organic phase was washed again with 500 ml of a solution of 50 g of sodium chloride in 500 ml of 1M hydrochloric acid
  4. washWashing with 500 ml of a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdrying over sodium sulphate and evaporation

Sources & evidence

ORD record
ord-6ef02a9af1754547b0fc70d9b1eb1fbd
Source dataset
uspto-grants-2014_08
Patent number
US08802860B2

Reaction notes

Loading…