Pyridine → Methyl 2-(4-chloroanilino)-2-oxoacetate

HRID 1979886Notes

Reaction equation

HRID 1979886 reaction equation
[Cl-].[C:2]([O:7][CH3:8])(=[O:6])[C:3]([O-])=[O:4].[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([NH:14][C:3](=[O:4])[C:2]([O:7][CH3:8])=[O:6])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 78124-ChloroanilineHCID 22574234Monomethyl oxalate chloride

Product 1

HCID 3584796Methyl 2-(4-chloroanilino)-2-oxoacetateYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

With stirring, 6.7 g of monomethyl oxalate chloride are added dropwise at 0° to 5° C. to a solution of 6.4 g of 4-chloroaniline and 7.9 g pyridine in 150 ml of dry methylene chloride. When the addition is complete, the suspension is stirred for 30 minutes at room temperature, then diluted with 100 ml of methylene chloride, washed twice with 3N hydrochloric acid and once with saturated sodium bicarbonate solution, dried and concentrated. The residual oil crystallises on trituration, affording 10.4 g of crystalline title compound with a melting point of 162°-164° C.

Workup

  1. additionWhen the addition
  2. stirringthe suspension is stirred for 30 minutes at room temperature
  3. washwashed twice with 3N hydrochloric acid and once with saturated sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residual oil crystallises on trituration

Sources & evidence

ORD record
ord-951e06a878cd42dba87a5f7b62b5f60b
Source dataset
uspto-grants-1984_11
Patent number
US04483707

Reaction notes

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