Borane → 3-(2-Hydroxyethyl)-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

HRID 2405010Notes

Reaction equation

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

Participants

Conditions

Temperature: 27 °C

Procedure

21.0 g (69.0 mmol) of [1-(2-methoxy-4-nitrophenyl)-2-oxo-1,2-dihydropyridin-3-yl]acetic acid were introduced as initial charge in 210 ml of THF, and 104 ml of 1M borane solution in THF were added dropwise at RT. The temperature increased to 27° C. during this addition. The reaction mixture was stirred overnight at RT. Following dilution with 400 ml of dichloromethane, 400 ml of 1N sodium hydroxide solution were added with cooling and the 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 17.0 g (85%) of crude product which were further reacted without purification.

Workup

additionwere added
temperaturewith cooling
stirringthe 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
customThis gave 17.0 g (85%) of crude product which were further reacted without purification

Sources & evidence

ORD record: ord-515a0a141e2749d9bfd393e2efcda06a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802860B2

Reaction notes

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