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

HRID 1619967Notes

Reaction equation

HRID 1619967 reaction equation
C([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]([CH3:22])[CH2:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:11][C:10]=1[OH:23])C1C=CC=CC=1.[H][H]>[Pd].CO>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]([CH3:22])[CH2:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:11][C:10]=1[OH:23]

Participants

5

Reactant 2

HCID 674671166-(4-benzylamino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 179934936-(4-amino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

43.0 g (139 mmol) 6-(4-benzylamino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one, 2.2 g of 10% palladium/charcoal and 400 ml of methanol are hydrogenated together for 24 h at RT and 3.45 bar of hydrogen pressure. The catalyst is filtered off and the filtrate is concentrated by rotary evaporation i. V., the residue is triturated with ethyl acetate, suction filtered and then dried at 50° C. in the vacuum dryer.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated by rotary evaporation i
  3. custom, the residue is triturated with ethyl acetate, suction
  4. filtrationfiltered
  5. customdried at 50° C. in the vacuum dryer

Sources & evidence

ORD record
ord-3cdd97063bad496ca269bb6d46ec3bbe
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

Loading…