Sodium borohydride → 4-Chloro-furo[3,4-c]quinolin-1(3H)-one

HRID 5130Notes

Reaction equation

HRID 5130 reaction equation
[Cl:1][C:2]1[C:11]2[C:12](=[O:16])[O:13][C:14](=[O:15])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[BH4-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:11]2[C:12](=[O:16])[O:13][CH2:14][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[Cl:1][C:2]1[C:11]2[CH2:12][O:13][C:14](=[O:15])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 541042384-Chloro-furo[3,4-c]quinoline-1,3-dione

Product 2

HCID 112067664-Chloro-furo[3,4-c]quinolin-1(3H)-oneHCID 57030353HCID 57030353, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a well stirred mixture of 4-Chloro-furo[3,4-c]quinoline-1,3-dione (1.9 g) in tetrahydrofuran (10 mL) was added sodium borohydride (400 mg) at 0° C. and stirring was continued for 2 h. The reaction was then quenched with excess 6N HCl and water, and concentrated in vacuo to afford 4-Chloro-furo[3,4-c]quinolin-3(1H)-one as a pink solid along with a small quantity of 4-Chloro-furo[3,4-c]quinolin-1(3H)-one which could be isolated by column chromatography on silica gel.

Workup

  1. stirringstirring
  2. customThe reaction was then quenched with excess 6N HCl and water
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdab9219ef3743deb64f5cb01f5301ba
Source dataset
uspto-grants-1993_09
Patent number
US05243049

Reaction notes

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