Hydrochloric Acid → 9-Hydroxy-9H-indeno[1,2-b]pyrazine-2,3(1H,4H)-dione

HRID 129446

Reaktionsgleichung

Reaktionsgleichung von HRID 129446
[NH:1]1[C:6](=[O:7])[C:5](=[O:8])[NH:4][C:3]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15](=[O:16])[C:2]1=2.O.[BH4-].[Na+].Cl>C(O)C>[OH:16][CH:15]1[C:2]2[NH:1][C:6](=[O:7])[C:5](=[O:8])[NH:4][C:3]=2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]1=2

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 4311764Sodium borohydrideHCID 190359779H-Indeno[1,2-b]pyrazine-2,3,9(1H,4H)-trione

Produkt 1

HCID 190359859-Hydroxy-9H-indeno[1,2-b]pyrazine-2,3(1H,4H)-dioneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred suspension of 9H-indeno[1,2-b]pyrazine-2,3,9(1H,4H)-trione. 1H2O (5.0 g, 21.5 mmol) in 200 ml of ethanol and 30 ml of water was added sodium borohydride (1.76 g, 46.5 mmol) in four portions over 2 hours, then 200 ml of water was added and the mixture was stirred for 18 hours at room temperature. The reaction mixture was acidified with hydrochloric acid (70 ml, 1N) to pH 1.5 and the precipitate was filtered off, washed with water and dried to give 4.59 g (91%) of the title compound. M.p. >300° C. 1H-NMR (DMSO-d6, δ): 5.1 (d, 1H), 5.72 (d, 1H), 7.15 (t, 1H), 7.28 (t, 1H), 7.41 (d, 1H), 7.48 (d, 1H), 12.0 (s, 1H), 12.25 (s, 1H).

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. washwashed with water
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c41c5b63054b47528ee23fd73a0170d4
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468748

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