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

HRID 263901

Reaction equation

HRID 263901 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-275b7c5c5f9040ba8403a9ee8f8a4d64
Source dataset
uspto-grants-1997_07
Patent number
US05646146

Linked notes

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