Dimethyl malonate → DIMETHYL 2-(4-CYANO-2-NITROPHENYL)MALONATE

HRID 552843Notes

Reaction equation

HRID 552843 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]([O:20][CH3:21])(=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16].[H-].[Na+]>CN(C=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH:14]([C:13]([O:20][CH3:21])=[O:19])[C:15]([O:17][CH3:18])=[O:16])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 7210838DIMETHYL 2-(4-CYANO-2-NITROPHENYL)MALONATEYield 39.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-3-nitrobenzonitrile (300 mg) and dimethyl malonate (286 mg) in DMF was added 60% NaH at 0° C., followed by reaction at room temperature to obtain dimethyl (4-cyano-2-nitrophenyl)malonate (198 mg).

Workup

  1. customfollowed by reaction at room temperature

Sources & evidence

ORD record
ord-cdd009e303604a62ac58b20525ca2b3f
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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