Sodium Hydroxide → HCID 178524410, compound

HRID 463353Notes

Reaction equation

HRID 463353 reaction equation
[Cl:1][CH:2]([Cl:23])[C:3]1[C:12]([C:13]([O:15]CC)=[O:14])=[C:11]([OH:18])[C:10]2[C:5](=[C:6]([C:19]([F:22])([F:21])[F:20])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[OH-].[Na+]>C(O)C>[Cl:23][CH:2]([Cl:1])[C:3]1[C:12]([C:13]([OH:15])=[O:14])=[C:11]([OH:18])[C:10]2[C:5](=[C:6]([C:19]([F:22])([F:20])[F:21])[CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178468961HCID 178468961, compound

Product 1

HCID 178524410HCID 178524410, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 22 g of the product of Step A, 220 ml of ethanol and 110 ml of sodium hydroxide was stirred at room temperature for 36 hours and the ethanol was then evaporated at less than 40° C. under reduced pressure. The solution was diluted with 200 ml of water and ice and the pH was adjusted to 1 by addition of concentrated hydrochloric acid. The mixture was vacuum filtered and the product was washed with water and then was dissolved in ether. The solution was filtered and the filtrate was dried and evaporated to dryness under reduced pressure to obtain 18 g of 2-dichloromethyl-4-hydroxy-8-trifluoromethyl-3-quinoline-carboxylic acid which was used as is for the next step.

Workup

  1. customthe ethanol was then evaporated at less than 40° C. under reduced pressure
  2. additionThe solution was diluted with 200 ml of water and ice
  3. additionthe pH was adjusted to 1 by addition of concentrated hydrochloric acid
  4. filtrationfiltered
  5. washthe product was washed with water
  6. dissolutionwas dissolved in ether
  7. filtrationThe solution was filtered
  8. customthe filtrate was dried
  9. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d7cc5ba3bb184cf18fccbb8832cc247b
Source dataset
uspto-grants-1985_05
Patent number
US04518775

Reaction notes

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