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

HRID 129446Notes

Reaction equation

HRID 129446 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-c41c5b63054b47528ee23fd73a0170d4
Source dataset
uspto-grants-1995_11
Patent number
US05468748

Reaction notes

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