Hydrochloric Acid → methyl 2-cyano-2-(2-nitrophenyl)acetate

HRID 970396Notes

Reaction equation

HRID 970396 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[H-].[Na+].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].Cl>CN(C=O)C>[C:1]([CH:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7747Methyl cyanoacetateHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 2779220methyl 2-cyano-2-(2-nitrophenyl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

6.3 A solution of 180 ml of methyl cyanoacetate in 300 ml of DMF is added dropwise at 0-50° with stirring and under a nitrogen atmosphere to a solution of 88 g of NaH suspension in 2 litres of DMF. The mixture is stirred for a further 30 minutes without cooling. A solution of 106 ml of o-fluoronitrobenzene in 100 ml of DMF is subsequently added dropwise, and the mixture is stirred at room temperature for a further 14 hours. The mixture is acidified using 10% HCl and subjected to conventional work-up, giving 165 g of methyl cyano(2-nitrophenyl)acetate (“FC”), m.p. 58-60°.

Workup

  1. temperaturewithout cooling
  2. stirringthe mixture is stirred at room temperature for a further 14 hours

Sources & evidence

ORD record
ord-be574b7da5444b5b90ce2b9739301fa2
Source dataset
uspto-grants-2007_12
Patent number
US07312224B2

Reaction notes

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