Triethylamine → HCID 178522689, compound

HRID 1155054Notes

Reaction equation

HRID 1155054 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.[F:7][C:8]([F:28])([F:27])[C:9]1[C:18]([C:19](Cl)=[O:20])=[C:17]([OH:22])[C:16]2[C:11](=[C:12]([C:23]([F:26])([F:25])[F:24])[CH:13]=[CH:14][CH:15]=2)[N:10]=1.C(N(CC)CC)C>C(OCC)(=O)C>[F:27][C:8]([F:7])([F:28])[C:9]1[C:18]([C:19]([NH:1][C:2]2[NH:6][N:5]=[N:4][N:3]=2)=[O:20])=[C:17]([OH:22])[C:16]2[C:11](=[C:12]([C:23]([F:26])([F:24])[F:25])[CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 178509299HCID 178509299, compoundHCID 178521117HCID 178521117, compound

Product 1

HCID 178522689HCID 178522689, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

5.03 g of anhydrous 5-amino-tetrazole were suspended with stirring at 8° C. in 230 ml of ethyl acetate and a solution of 21.9 g of 2,8-bis-(trifluoromethyl)-4-hydroxy-3-quinoline-carboxylic acid chloride in 230 ml of ethyl acetate and a solution of 18 g of triethylamine in 180 ml of ethyl acetate were simultaneously added to the reaction mixture over 15 minutes. The mixture returned to room temperature and was refluxed for one hour and cooled. The mixture was vacuum filtered and the recovered product was dissolved in one liter of water. The filtrate wash waters were added to the solution and the pH was adjusted to 1 by addition of 20% hydrochloric acid. The mixture was vacuum filtered and the recovered product was dissolved in 50 ml of 2 N sodium hydroxide. 150 ml of water were added to the solution and the mixture was heated to reflux and cooled. The mixture was acidified with 100 ml of 20% hydrochloric acid and was vacuum filtered. The product was dried and crystallized from 250 ml of acetic acid to obtain 12.279 g of 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(1H-tetrazol-5-yl)-3-quinolinecarboxamide melting at >260° C.

Workup

  1. customreturned to room temperature
  2. temperaturewas refluxed for one hour
  3. temperaturecooled
  4. filtrationfiltered
  5. dissolutionthe recovered product was dissolved in one liter of water
  6. washThe filtrate wash waters
  7. additionwere added to the solution
  8. additionthe pH was adjusted to 1 by addition of 20% hydrochloric acid
  9. filtrationfiltered
  10. dissolutionthe recovered product was dissolved in 50 ml of 2 N sodium hydroxide
  11. addition150 ml of water were added to the solution
  12. temperaturethe mixture was heated
  13. temperatureto reflux
  14. temperaturecooled
  15. filtrationfiltered
  16. customThe product was dried
  17. customcrystallized from 250 ml of acetic acid

Sources & evidence

ORD record
ord-9fe0534f781f421e8442c59701f29c52
Source dataset
uspto-grants-1981_11
Patent number
US04299831

Reaction notes

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