3,4,5-Trichloroaniline → HCID 19735172, compound

HRID 326629Notes

Reaction equation

HRID 326629 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:10])[C:8]=1[Cl:9])[NH2:5].[CH3:11][O:12][C:13]([C:15]#[C:16][C:17](OC)=[O:18])=[O:14]>CO.CCCCCC>[Cl:1][C:2]1[C:8]([Cl:9])=[C:7]([Cl:10])[CH:6]=[C:4]2[C:3]=1[C:17](=[O:18])[CH:16]=[C:15]([C:13]([O:12][CH3:11])=[O:14])[NH:5]2

Participants

5

Reactant 2

HCID 124693,4,5-TrichloroanilineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 19735172HCID 19735172, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
240 °C

Procedure

3,4,5-Trichloroaniline (25 g, 0.127 mol) and dimethylacetylene dicarboxylate (10.9 ml, 0.12 mol) were dissolved in dry methanol (300 ml) at 0° C. then heated at reflux for 14 h. The mixture was allowed to cool, then diluted with hexane (200 ml) and the yellow solid which precipated was collected by filtration and heated in diphenyl ether (200 ml) at 240° C. for 10 minutes. The reaction mixture was allowed to cool to room temperature and diluted with hexane. The solid which deposited was collected and recrystallised from acetone (500 ml) to give methyl 5,6,7-trichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate (11.91 g), m.p. 295°-296° C. (decomp), δ (360 MHz, DMSO-d6) 3.96 (3H, s, CH3), 6.63 (1H, s, 3-H) and 8.17 (1H, s, 8-H) (Found C, 43.09; H, 1.70; N, 4.47%, C11H16NO3Cl3 requires C, 43.10; H, 1.97; N, 4.57%).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 14 h
  3. temperatureto cool
  4. filtrationthe yellow solid which precipated was collected by filtration
  5. temperatureto cool to room temperature
  6. additiondiluted with hexane
  7. customThe solid which deposited was collected
  8. customrecrystallised from acetone (500 ml)

Sources & evidence

ORD record
ord-7adf59027a1d4dd584d555825185b529
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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