Hydrochloric Acid → HCID 135773202, compound

HRID 904700Notes

Reaction equation

HRID 904700 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=[C:7]2Cl)(=[O:3])[CH3:2].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:30]1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>C(O)C>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH2:21][CH3:30])=[O:19])[CH:8]=[C:7]2[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 6115Aniline2×HCID 136035444HCID 136035444, compound

Product 1

HCID 135773202HCID 135773202, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 6-acetyl-4-chloro-7-hydroxy-8-propyl-quinoline-2-carboxylate (1.5 g) was treated with aniline (20 ml) at 175° C. in an autoclave in the presence of p-toluene sulphonic acid (0.1 g) for 72 hours. On cooling the aniline was removed and the residue was heated on a steambath for 12 hours with 70% sulphuric acid. The reaction mixture was poured onto crushed ice and neutralised with ammonia solution to pH 7. Extraction with ethyl acetate followed by drying and evaporation afforded a gum which was taken up in dry ethanol and saturated with hydrogen chloride gas while refluxing for 1 hour. Evaporation of the solvent and trituration with ether afforded the sub-title compound (0.37 g) identified by NMR and mass spectroscopy.

Workup

  1. customwas removed
  2. temperaturethe residue was heated on a steambath for 12 hours with 70% sulphuric acid
  3. additionThe reaction mixture was poured
  4. customonto crushed ice
  5. extractionExtraction with ethyl acetate
  6. customby drying
  7. customevaporation
  8. customafforded a gum which
  9. temperaturewhile refluxing for 1 hour
  10. customEvaporation of the solvent and trituration with ether

Sources & evidence

ORD record
ord-17e88fe05b364b8fa3a42696ab28d775
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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