3-Chloroaniline → HCID 178522043, compound

HRID 1155053Notes

Reaction equation

HRID 1155053 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[F:16][C:17]([F:37])([F:36])[C:18]1[C:27]([C:28](Cl)=[O:29])=[C:26]([OH:31])[C:25]2[C:20](=[C:21]([C:32]([F:35])([F:34])[F:33])[CH:22]=[CH:23][CH:24]=2)[N:19]=1>C(OCC)(=O)C.[OH-].[Na+]>[F:36][C:17]([F:16])([F:37])[C:18]1[C:27]([C:28]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=2)=[O:29])=[C:26]([OH:31])[C:25]2[C:20](=[C:21]([C:32]([F:35])([F:33])[F:34])[CH:22]=[CH:23][CH:24]=2)[N:19]=1

Participants

6

Reactant 3

HCID 79323-ChloroanilineHCID 8471TriethylamineHCID 178521117HCID 178521117, compound

Product 1

HCID 178522043HCID 178522043, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4.083 g of m-chloroaniline, 9.71 g of triethylamine and 65 ml of ethyl acetate was poured over 15 minutes at 8° C.-10° C. into a solution of 11.96 g of 2,8-bis-(trifluoromethyl)-4-hydroxy-3-quinoline-carboxylic acid chloride in 130 ml of ethyl acetate with violent stirring and the temperature was allowed to return to room temperature. The mixture was refluxed for one hour and was cooled and vacuum filtered. The filtrate was washed with water, was dried and evaporated to dryness at 40° C. under reduced pressure to obtain 17.14 g of a triethylamine salt. The residue was dissolved in 2 N sodium hydroxide solution which was then heated to reflux and cooled to room temperature. The mixture was vacuum filtered and the recovered product was dissolved in water. The solution was adjusted to a pH of 1 by addition of 20% hydrochloric acid and the mixture was vacuum filtered. The recovered product was crystallized from benzene to obtain 7.599 g of 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(3-chlorophenyl)-3-quinolinecarboxamide melting at 152° C.

Workup

  1. customto return to room temperature
  2. temperatureThe mixture was refluxed for one hour
  3. temperaturewas cooled
  4. filtrationvacuum filtered
  5. washThe filtrate was washed with water
  6. customwas dried
  7. customevaporated to dryness at 40° C. under reduced pressure
  8. customto obtain 17.14 g of a triethylamine salt
  9. temperaturewas then heated
  10. temperatureto reflux
  11. filtrationfiltered
  12. dissolutionthe recovered product was dissolved in water
  13. additionThe solution was adjusted to a pH of 1 by addition of 20% hydrochloric acid
  14. filtrationfiltered
  15. customThe recovered product was crystallized from benzene

Sources & evidence

ORD record
ord-44bfbdf56a5446859e340eb2de5a9678
Source dataset
uspto-grants-1981_11
Patent number
US04299831

Reaction notes

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