Borane → 1-(2,6-Dimethyl-4-nitrophenyl)-3-(2-hydroxyethyl)pyridin-2(1H)-one

HRID 2405020Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19](O)=[O:20])[C:13]1=[O:22].B>C1COCC1.ClCCl.[OH-].[Na+]>[CH3:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([CH3:1])[C:3]=1[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][OH:20])[C:13]1=[O:22]

Participants

Conditions

Temperature: 27 °C

Procedure

26.5 g (87.7 mmol) of [1-(2,6-dimethyl-4-nitrophenyl)-2-oxo-1,2-dihydropyridin-3-yl]acetic acid were introduced as initial charge in 265 ml of THF at RT. 132 ml of 1M borane solution in THF (132 mmol) were added dropwise. During this addition, the temperature increased to 27° C. The reaction mixture was stirred for 1 h at RT and then the same amount of borane solution was added. The reaction mixture was stirred overnight at RT. It was diluted with 500 ml of dichloromethane, and 500 ml of 1N sodium hydroxide solution were added with cooling. The reaction mixture was stirred for 30 min, the phases were separated and the organic phase was washed with water, dried over sodium sulphate, filtered and evaporated to dryness on a rotary evaporator. This gave 12.6 g (48%) of the desired product as crystalline solid.

Workup

additionDuring this addition
stirringThe reaction mixture was stirred overnight at RT
additionwere added
temperaturewith cooling
stirringThe reaction mixture was stirred for 30 min
customthe phases were separated
washthe organic phase was washed with water
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated to dryness on a rotary evaporator

Sources & evidence

ORD record: ord-87f677aad42148b491b9458bc621e1d0
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802860B2

Reaction notes

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