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

HRID 1451288Notes

Reaction equation

HRID 1451288 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-9f75cc2cae504e3ca40d0c3d04f50ebd
Source dataset
uspto-grants-1997_02
Patent number
US05604235

Reaction notes

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