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

HRID 1415714Notes

Reaction equation

HRID 1415714 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-Chlorofuro[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-be038762e9c746a188cbd73dc99f2c13
Source dataset
uspto-grants-1999_06
Patent number
US05908932

Reaction notes

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