HCID 178468890, compound → HCID 178439957, compound

HRID 2419816Notes

Reaction equation

HRID 2419816 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH:16]([CH3:18])[CH3:17])[C:3]=1[C:19]([O:21]CC)=[O:20]>C(O)C>[OH:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:13])[F:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH:16]([CH3:18])[CH3:17])[C:3]=1[C:19]([OH:21])=[O:20]

Participants

3

Reactant 1

HCID 178468890HCID 178468890, compound

Product 1

HCID 178439957HCID 178439957, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 14 g of the product of Step D, 75 ml of 36° Be sodium hydroxide and 150 ml of ethanol was refluxed for 6 hours and was then cooled. The ethanol was distilled and 150 ml of ice water were added. The mixture was washed with methylene chloride and was acidified with slow addition of 2N hydrochloric acid at less than 15° C. The mixture was filtered and washed until the wash waters had a pH of 6 to obtain 6.9 g of 4-hydroxy-2-isopropyl-8-trifluoromethyl-quinoline-3-carboxylic acid melting at 204° C which was used as is for the next step.

Workup

  1. temperaturewas then cooled
  2. distillationThe ethanol was distilled
  3. addition150 ml of ice water were added
  4. washThe mixture was washed with methylene chloride
  5. additionwas acidified with slow addition of 2N hydrochloric acid at less than 15° C
  6. filtrationThe mixture was filtered
  7. washwashed until the wash waters

Sources & evidence

ORD record
ord-68997b91621b4f7494e26a51c0b39010
Source dataset
uspto-grants-1978_08
Patent number
US04107310

Reaction notes

Loading…