6-(4-benzylamino-3-hydroxy-phenyl)-5-ethyl-4-methyl-4,5-dihydro-2H-pyridazin-3-one → 6-(4-amino-3-hydroxy-phenyl)-5-ethyl-4-methyl-4,5-dihydro-2H-pyridazin-3-one

HRID 1619935Notes

Reaction equation

HRID 1619935 reaction equation
C([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]([CH2:23][CH3:24])[CH:17]([CH3:22])[C:18](=[O:21])[NH:19][N:20]=2)=[CH:11][C:10]=1[OH:25])C1C=CC=CC=1>[Pd].CO>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]([CH2:23][CH3:24])[CH:17]([CH3:22])[C:18](=[O:21])[NH:19][N:20]=2)=[CH:11][C:10]=1[OH:25]

Participants

4

Reactant 1

HCID 674646956-(4-benzylamino-3-hydroxy-phenyl)-5-ethyl-4-methyl-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 674628516-(4-amino-3-hydroxy-phenyl)-5-ethyl-4-methyl-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.20 g (6.52 mmol) 6-(4-benzylamino-3-hydroxy-phenyl)-5-ethyl-4-methyl-4,5-dihydro-2H-pyridazin-3-one, 120 mg 10% Pd/C and 20 mL MeOH are hydrogenated for 2 h at 3 bar H2. The reaction mixture is concentrated by rotary evaporation i. V. and the residue is crystallised with acetonitrile/diethyl ether.

Workup

  1. concentrationThe reaction mixture is concentrated by rotary evaporation i
  2. customand the residue is crystallised with acetonitrile/diethyl ether

Sources & evidence

ORD record
ord-1a1380be7ccb494981d4b4b282da17ee
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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