Water → HCID 178522559, compound

HRID 1982594Notes

Reaction equation

HRID 1982594 reaction equation
B(Br)(Br)Br.[OH:5][C:6]1[C:15]2[C:10](=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH2:20][O:21]C)[C:7]=1[C:23]([NH:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1)=[O:24].O>C(Cl)Cl>[OH:5][C:6]1[C:15]2[C:10](=[C:11]([C:16]([F:17])([F:19])[F:18])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH2:20][OH:21])[C:7]=1[C:23]([NH:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1)=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 178494648HCID 178494648, compound

Product 1

HCID 178522559HCID 178522559, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4 ml of boron tribromide in 30 ml of methylene chloride was added with stirring at -70° C. to a solution of 2.88 g of the product of Example 3 in 75 ml of methylene chloride and the mixture stood overnight with stirring while the temperature was allowed to rise to -20° C. The mixture was poured into 500 ml of ice and water and the mixture was stirred for 20 minutes and was vacuum filtered. The product was washed with water until the pH was 5 to 6 and was dried under reduced pressure at 100° C. The product was dissolved in refluxing dimethylformamide and the solution was cooled, iced and vacuum filtered. The product was washed with dimethylformamide and then with ether and dried under reduced pressure at 120° C. to obtain 2.3 g of 4-hydroxy-2-hydroxymethyl-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide melting at 280° C.

Workup

  1. customto rise to -20° C
  2. stirringthe mixture was stirred for 20 minutes
  3. filtrationfiltered
  4. washThe product was washed with water until the pH was 5 to 6
  5. customwas dried under reduced pressure at 100° C
  6. dissolutionThe product was dissolved
  7. temperaturein refluxing dimethylformamide
  8. temperaturethe solution was cooled
  9. filtrationiced and vacuum filtered
  10. washThe product was washed with dimethylformamide
  11. dry with materialwith ether and dried under reduced pressure at 120° C.

Sources & evidence

ORD record
ord-5e247a03853e47859ae9a99ef88bdae7
Source dataset
uspto-grants-1986_06
Patent number
US04596875

Reaction notes

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