Water → 8-Hydroxymethyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 1359563

反応式

HRID 1359563 の反応式
[CH:1]([C:3]1[CH2:9][C:8]2[CH:10]=[C:11]3[O:16][CH2:15][O:14][C:12]3=[CH:13][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:5][N:4]=1)=[O:2].O.B([O-])=O.[Na+]>C1COCC1>[OH:2][CH2:1][C:3]1[CH2:9][C:8]2[CH:10]=[C:11]3[O:16][CH2:15][O:14][C:12]3=[CH:13][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:5][N:4]=1

参加物

5

反応物 3

HCID 962WaterHCID 145326Sodium metaborateHCID 108930778-formyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

生成物 1

HCID 181831918-Hydroxymethyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine収率 78.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

2.5 g (7.41 mmol) of 8-formyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (I, stage A) is suspended in THF:water=1:1 and mixed with 0.14 g (3.7 mmol) of sodium boranate while being stirred and cooled to 20° C. After 45 minutes of stirring, it is filtered and the crude product is precipitated from the filtrate with 130 ml of water. 2.35 g, which is recrystallized from a mixture of 6.3 ml of dimethylformamide and 1.3 ml of water, is obtained. 1.97 g (78%) of the title compound with a melting point of 175° C. (decomposition) is obtained.

後処理

  1. stirringAfter 45 minutes of stirring
  2. filtrationit is filtered
  3. customthe crude product is precipitated from the filtrate with 130 ml of water
  4. custom2.35 g, which is recrystallized from a mixture of 6.3 ml of dimethylformamide and 1.3 ml of water
  5. customis obtained

出典と根拠

ORDレコード
ord-53cc19ebc4ab4e9983c0880dc0bc2169
出典データセット
uspto-grants-2003_07
特許番号
US06600036B2

関連ノート

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