Sodium borohydride → 1-Benzyl-5-chloro-3-methylcinnolin-4(1H)-one

HRID 598158Notes

Reaction equation

HRID 598158 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH2:20]Cl)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CS(C)=O.O>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH3:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 672675101-Benzyl-5-chloro-3-chloromethylcinnolin-4(1H)-one

Product 1

HCID 672671161-Benzyl-5-chloro-3-methylcinnolin-4(1H)-oneYield 92.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To 0.170 g (0.53 mmol) of 1-benzyl-5-chloro-3-chloromethylcinnolin-4(1H)-one in 6 mL of dimethylsulfoxide was added 0.050 g (1.3 mmol) of sodium borohydride. The reaction was stirred at room temperature for 3 h and diluted with water. The resulting precipitate was collected and dried to give 0.140 g (92%) of the title compound as a fluffy cream colored solid.

Workup

  1. customThe resulting precipitate was collected
  2. customdried

Sources & evidence

ORD record
ord-8ae9eae1c61941d59b07433cd3ce076b
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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