Hydrochloric Acid → 6-(3,4-Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

HRID 1190935Notes

Reaction equation

HRID 1190935 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[N+:23]([O-])=O)C1C=CC=CC=1.CO.Cl>[Pd].O>[NH2:23][C:10]1[CH:11]=[C:12]([C:15]2[CH:16]([CH3:22])[CH2:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:13]=[CH:14][C:9]=1[NH2:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 117246806-(4-benzylamino-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 34410526-(3,4-Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

6-(4-Benzylamino-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one was mixed with methanol and a separately prepared mixture of Pd/C catalyst, water and hydrochloric acid. After hydrogenation, the reaction mixture was filtered and the filtrate was alkalined with a sodium hydroxide solution. The precipitate was filtered, rinsed with water and methanol, filtered and dried, to obtain 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one.

Workup

  1. filtrationAfter hydrogenation, the reaction mixture was filtered
  2. filtrationThe precipitate was filtered
  3. washrinsed with water and methanol
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-1937f481303a4a6bafdb2957ec685339
Source dataset
uspto-grants-2014_03
Patent number
US08680101B2

Reaction notes

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