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

HRID 430648

Reaction equation

HRID 430648 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-999dd10ad7a0469f92ee27c353b9f1d3
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Linked notes

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