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

HRID 1359563

Reaktionsgleichung

Reaktionsgleichung von HRID 1359563
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 181831918-Hydroxymethyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepineAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-53cc19ebc4ab4e9983c0880dc0bc2169
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06600036B2

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