Sodium Hydroxide → (R)-6-(4-hydrazino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one
Reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C@H:13]([CH3:19])[CH2:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>O.Cl>[NH:5]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C@H:13]([CH3:19])[CH2:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1)[NH2:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A slight modification on the procedure described in J.Med.Chem. (1990), 33(10), 2870-2875 was used as follows. A solution of sodium nitrite (1.7 g) in water (12.5 ml) was added slowly at 0-5° C. to a solution of (R)-6-(4-aminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one (5 g) in 1 M hydrochloric acid (75 ml). The resulting solution was stirred on ice bath for five minutes and then added slowly to a solution of tin(II)chloride dihydrate (17 g) in 1 M hydrochloric acid (150 ml) keeping the reaction temperature below 5° C. This solution was stirred on ice for forty minutes and then a solution of 50% NaOH (75 ml) was quickly added. The resulting mixture was stirred on ice bath until the temperature reached zero degrees Celsius. The crystals were filtered and washed with dilute ammonia. Yield: 5.0 g, 93%.
Workup
- customthe reaction temperature below 5° C
- stirringThis solution was stirred on ice for forty minutes
- stirringThe resulting mixture was stirred on ice bath until the temperature
- customreached zero degrees Celsius
- filtrationThe crystals were filtered
- washwashed with dilute ammonia
Sources & evidence
- ORD record
- ord-036ea9b989af47d9945eeb715a41bb5a
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699868B2
Reaction notes
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