3-(2-Hydroxyethyl)-1-{4-nitro-2-[(1E)-prop-1-en-1-yl]phenyl}pyridin-2(1H)-one → 1-(4-Amino-2-propyl phenyl)-3-(2-hydroxyethyl)pyridin-2(1H)-one

HRID 452237Notes

Reaction equation

HRID 452237 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5](=[O:22])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=2/[CH:19]=[CH:20]/[CH3:21])[CH:7]=[CH:8][CH:9]=1.[H][H]>C1COCC1.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([N:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][CH2:2][OH:1])[C:5]2=[O:22])=[C:11]([CH2:19][CH2:20][CH3:21])[CH:12]=1

Participants

5

Reactant 2

HCID 595366073-(2-Hydroxyethyl)-1-{4-nitro-2-[(1E)-prop-1-en-1-yl]phenyl}pyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 595366101-(4-Amino-2-propyl phenyl)-3-(2-hydroxyethyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

520 mg (1.73 mmol) of the compound from Example 46A are dissolved in 10 ml of THF. 30 mg of palladium on carbon are added, and the mixture is hydrogenated at RT in a hydrogen atmosphere under atmospheric pressure. The mixture is then filtered through kieselguhr, 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. This gives 471 mg (89% of theory) of the desired product.

Workup

  1. filtrationThe mixture is then filtered through kieselguhr
  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-e4fe05ddb33f4d29a97eb634e14e236c
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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