3-Chloroaniline → HCID 69515221, compound

HRID 1353325Notes

Reaction equation

HRID 1353325 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([C:16](OCC)=[O:17])#[C:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>CO.C1(OC2C=CC=CC=2)C=CC=CC=1.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:6]([C:16](=[O:17])[CH2:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:5]2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 79323-ChloroanilineHCID 69803Diethyl acetylenedicarboxylate

Product 1

HCID 69515221HCID 69515221, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 7583Diphenyl EtherSolventHCID 8058HexaneSolvent

Procedure

3-Chloroaniline (28.5 g, 200 mmol) and diethyl acetylenedicarboxylate (37.4 g, 220 mmol) are heated in MeOH (300 mL) for 3 h at reflux. The reaction mixture is concentrated to yield a yellow residue, which is heated in phenyl ether (400 mL), for ¾ h. The mixture is cooled to room temp. and diluted with hexane whereupon a white solid precipitates which is filtered off: 34.4 g.

Workup

  1. temperatureat reflux
  2. concentrationThe reaction mixture is concentrated
  3. customto yield a yellow residue, which
  4. temperatureThe mixture is cooled to room temp.
  5. customprecipitates which
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-27c268b881fc4a9fa4a723a49dcbdcd9
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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