3-(3-Hydroxypropyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one → 1-(4-Amino-2-methylphenyl)-3-(3-hydroxypropyl)pyridin-2(1H)-one

HRID 452240Notes

Reaction equation

HRID 452240 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:6](=[O:21])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=2[CH3:20])[CH:8]=[CH:9][CH:10]=1.[H][H]>C1COCC1.[Pd]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([N:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][CH2:3][CH2:2][OH:1])[C:6]2=[O:21])=[C:12]([CH3:20])[CH:13]=1

Participants

5

Reactant 2

HCID 594101913-(3-Hydroxypropyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 594102141-(4-Amino-2-methylphenyl)-3-(3-hydroxypropyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

475 mg (1.65 mmol) of the compound from Example 49A are dissolved in 48 ml of THF. 50 mg (0.05 mmol) of palladium on carbon are then added, and the mixture is hydrogenated at RT in a hydrogen atmosphere under atmospheric pressure. The mixture is then filtered, the filter cake is washed three times with THF and the filtrate is freed from the solvent. The reaction product is reacted further without further purification.

Workup

  1. filtrationThe mixture is then filtered
  2. washthe filter cake is washed three times with THF
  3. customThe reaction product is reacted further without further purification

Sources & evidence

ORD record
ord-439abc16f89643e99f2e5c69b5ccec81
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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