Sodium Hydroxide → HCID 178524537, compound

HRID 1155056Notes

Reaction equation

HRID 1155056 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[C:12]([C:13]([O:15]CC)=[O:14])=[C:11]([OH:18])[C:10]2[C:5](=[CH:6][C:7]([C:19]([F:22])([F:21])[F:20])=[CH:8][CH:9]=2)[N:4]=1.[OH-].[Na+]>C(O)C>[F:23][C:2]([F:1])([F:24])[C:3]1[C:12]([C:13]([OH:15])=[O:14])=[C:11]([OH:18])[C:10]2[C:5](=[CH:6][C:7]([C:19]([F:22])([F:20])[F:21])=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178469126HCID 178469126, compound

Product 1

HCID 178524537HCID 178524537, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 21.38 g of the product of Step D, 300 ml of ethanol and 60.5 ml of sodium hydroxide solution was refluxed with stirring for 7 hours and the ethanol was then distilled under reduced pressure at 40° C. The residue was taken up in about 300 ml of water and the pH was adjusted to 1 by addition of 20% hydrochloric acid. The mixture was vacuum filtered and the recovered product was washed with water and was taken up in 350 ml of ether. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure to obtain 18.65 g of 2,7-bis-(trifluoromethyl)-4-hydroxy-3-quinoline-carboxylic acid melting at 240° C.

Workup

  1. temperaturewas refluxed
  2. distillationthe ethanol was then distilled under reduced pressure at 40° C
  3. additionthe pH was adjusted to 1 by addition of 20% hydrochloric acid
  4. filtrationfiltered
  5. washthe recovered product was washed with water
  6. washThe organic phase was washed with water
  7. customdried
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0eb840adc613495c94837baa77c92c21
Source dataset
uspto-grants-1981_11
Patent number
US04299831

Reaction notes

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