Hydrochloric Acid → HCID 178446991, compound

HRID 1153813Notes

Reaction equation

HRID 1153813 reaction equation
[CH2:1]([CH:5]1[C:9]2=[N:10][C:11]3[C:12]([C:19]([F:22])([F:21])[F:20])=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]([OH:18])=[C:8]2[C:7](=[N:23][C:24]2[S:25][CH:26]=[CH:27][N:28]=2)[O:6]1)[CH2:2][CH2:3][CH3:4].Cl.[OH2:30]>>[OH:18][C:17]1[C:16]2[C:11](=[C:12]([C:19]([F:22])([F:20])[F:21])[CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([CH:5]([OH:30])[CH2:1][CH2:2][CH2:3][CH3:4])[C:8]=1[C:7]([NH:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1)=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178442015HCID 178442015, compound

Product 1

HCID 178446991HCID 178446991, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 6.1 g of the product of Step C, 60 ml of water and 60 ml of 6N hydrochloric acid was heated at 50° C. for 5 hours and was then cooled to room temperature and iced and vacuum filtered. The product was washed with water and added to 100 ml of water. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried, filtered and evaporated to dryness under reduced pressure. The 6.4 of residue was added to 50 ml of ether and the mixture was iced and vacuum filtered. The product was washed with ether and dried under reduced pressure at 60° C. to obtain 3.9 g of 4-hydroxy-2-(1-hydroxypentyl)-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide melting at 190° C.

Workup

  1. temperaturewas then cooled to room temperature
  2. filtrationiced and vacuum filtered
  3. washThe product was washed with water
  4. additionadded to 100 ml of water
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic phase was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure
  10. additionThe 6.4 of residue was added to 50 ml of ether
  11. filtrationvacuum filtered
  12. washThe product was washed with ether
  13. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-dcaca0f64c224484886f67c8aac3d5a1
Source dataset
uspto-grants-1984_12
Patent number
US04486438

Reaction notes

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