Pyridine → Methyl [3-(3-bromopropoxy)anilino](oxo)acetate

HRID 1607163Notes

Reaction equation

HRID 1607163 reaction equation
[Cl-].[CH3:2][O:3][C:4](=[O:8])[C:5]([OH:7])=O.[Br:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].N1C=CC=CC=1>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:8])[C:5]([NH:17][C:16]1[CH:18]=[CH:19][CH:20]=[C:14]([O:13][CH2:12][CH2:11][CH2:10][Br:9])[CH:15]=1)=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4592563-(3-Bromopropoxy)-anilineHCID 86640482Oxalic acid monomethyl ester chloride

Product 1

HCID 19818630Methyl [3-(3-bromopropoxy)anilino](oxo)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.5 ml of oxalic acid monomethyl ester chloride in 10 ml of methylene chloride is added dropwise in the course of 10 minutes to a solution of 3.5 g of 3-(3-bromopropoxy)-aniline and 1.3 ml of pyridine in 40 ml of methylene chloride. After stirring for 2 hours at room temperature the mixture is poured onto water and extracted with methylene chloride. The combined extracts are concentrated by evaporation and the residue is chromatographed with methylene chloride/ethyl acetate (10:1) over silica gel. The eluate is concentrated by evaporation and the residue is crystallised from ether/hexane. N-[3-(3-bromopropoxy)-phenyl]-oxamic acid methyl ester having a melting point of 90°-91° is obtained.

Workup

  1. additionis poured onto water
  2. extractionextracted with methylene chloride
  3. concentrationThe combined extracts are concentrated by evaporation
  4. customthe residue is chromatographed with methylene chloride/ethyl acetate (10:1) over silica gel
  5. concentrationThe eluate is concentrated by evaporation
  6. customthe residue is crystallised from ether/hexane

Sources & evidence

ORD record
ord-07b00e73ef974edd9da99324f6532f2c
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

Loading…