HCID 178468992, compound → HCID 178437488, compound

HRID 2419811Notes

Reaction equation

HRID 2419811 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]([CH2:16][CH3:17])[C:3]=1[C:18]([O:20]CC)=[O:19]>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]([CH2:16][CH3:17])[C:3]=1[C:18]([OH:20])=[O:19]

Participants

3

Reactant 1

HCID 178468992HCID 178468992, compound

Product 1

HCID 178437488HCID 178437488, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5 g of the product of Step D in 25 ml of 36° Be sodium hydroxide solution and 50 ml of ethanol was refluxed for 31/2 hours and was then cooled. The ethanol was evaporated and 100 ml of ice water were added thereto. The mixture was washed with methylene chloride and was acidified slowly by addition of 2N hydrochloric acid under 15° C. The mixture was filtered and the filtrate was washed with water until the wash water pH was 6 to obtain 4.4 g of 4-hydroxy-2-ethyl-8-trifluoromethyl-quinoline-3-carboxylic acid melting at 174° C which was used as is for the next step.

Workup

  1. temperaturewas then cooled
  2. customThe ethanol was evaporated
  3. addition100 ml of ice water were added
  4. washThe mixture was washed with methylene chloride
  5. additionwas acidified slowly by addition of 2N hydrochloric acid under 15° C
  6. filtrationThe mixture was filtered
  7. washthe filtrate was washed with water until the wash water pH was 6

Sources & evidence

ORD record
ord-b9fd9b4c85064e07b6c5ac9a3abcf0a5
Source dataset
uspto-grants-1978_08
Patent number
US04107310

Reaction notes

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