Dimethylamine → HCID 135773205, compound

HRID 904696Notes

Reaction equation

HRID 904696 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]C)=[O:19])[CH:8]=[C:7]2Cl)(=[O:3])[CH3:2].[CH3:23][NH:24][CH3:25].O>CO.S(=O)(=O)(O)O>[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]([OH:20])=[O:19])[CH:8]=[C:7]2[N:24]([CH3:25])[CH3:23])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 136035444HCID 136035444, compound

Product 1

HCID 135773205HCID 135773205, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

Methyl 6-acetyl-4-chloro-7-hydroxy-8-propyl-quinoline-2-carboxylate (6 g; 18.6474 mmole) in 33% w/w dimethylamine in methanol (50 ml) was heated at 100° C. under pressure (autoclaved) for 24 hours. The mixture was cooled, and treated with water, concentrated, and extracted with chloroform. The extract was washed with water, dried and evaporated to give a brown solid. The solid was heated in 70% sulphuric acid (150 ml) on a steambath for 6 hours. The mixture was cooled and the pH adjusted to about 7 before extraction into chloroform. The extract was dried and evaporated to give a yellow solid (1.25 g). NMR and mass spectra were consistent with the required structure.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated
  7. customto give a brown solid
  8. temperatureThe mixture was cooled
  9. extractionthe pH adjusted to about 7 before extraction into chloroform
  10. customThe extract was dried
  11. customevaporated

Sources & evidence

ORD record
ord-724ebbfb9e304b0585e4f859b7c7652d
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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