Pyridine → HCID 19818641, compound

HRID 1607164Notes

Reaction equation

HRID 1607164 reaction equation
[CH3:1][O:2][C:3](=[O:7])[C:4](Cl)=[O:5].[NH2:8][C:9]1[CH:10]=[C:11]([O:15][CH3:16])[CH:12]=[CH:13][CH:14]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:7])[C:4]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 108243-MethoxyanilineHCID 79846Methyl chloroglyoxylate

Product 1

HCID 19818641HCID 19818641, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.9 ml of chloro-oxalic acid methyl ester in 10 ml of methylene chloride is added dropwise in the course of 10 minutes to a solution of 2.5 g of 3-aminoanisole and 1.5 ml of pyridine in 40 ml of methylene chloride. After stirring for 3 hours at room temperature the mixture is poured onto water and extracted with methylene chloride. The extracts are dried over sodium sulphate, concentrated by evaporation and crystallised from ether/hexane. N-(3-methoxyphenyl)-oxamic acid methyl ester is obtained.

Workup

  1. additionis poured onto water
  2. extractionextracted with methylene chloride
  3. dry with materialThe extracts are dried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. customcrystallised from ether/hexane

Sources & evidence

ORD record
ord-f903608ad24544f989ef4a746217148c
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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