Sodium Hydroxide → (R)-6-(4-hydrazino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

HRID 47266노트

반응식

HRID 47266 반응식
[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]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 10465484(R)-6-(4-Aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-oneHCID 23668193Sodium Nitrite

생성물 1

HCID 69529174(R)-6-(4-hydrazino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매2회HCID 962Water용매

실험 절차

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%.

후처리

  1. customthe reaction temperature below 5° C
  2. stirringThis solution was stirred on ice for forty minutes
  3. stirringThe resulting mixture was stirred on ice bath until the temperature
  4. customreached zero degrees Celsius
  5. filtrationThe crystals were filtered
  6. washwashed with dilute ammonia

출처 및 근거

ORD 기록
ord-036ea9b989af47d9945eeb715a41bb5a
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699868B2

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