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

HRID 47266ノート

反応式

HRID 47266 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒2 回HCID 962Water溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-036ea9b989af47d9945eeb715a41bb5a
出典データセット
uspto-grants-2004_03
特許番号
US06699868B2

反応ノート

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