Hydrochloric Acid → HCID 18002696, compound

HRID 1384884Notes

Reaction equation

HRID 1384884 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][Si](C(C)(C)C)(C)C)=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:20]([F:23])([F:22])[F:21])=[N:7]2.Cl.O>CO>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:20]([F:21])([F:22])[F:23])=[N:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 18002687HCID 18002687, compound

Product 1

HCID 18002696HCID 18002696, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 5-bromo-8-(tert-butyldimethylsilanyloxy)-2-trifluoromethylquinoline (21 g) in methanol (150 ml) was treated with 37% hydrochloric acid solution (5 ml) and water (5 ml). The mixture was stirred for 12 h at room temperature and at 45° C. for 2 h. The methanol was removed in vacuo and the residue partitioned between 10% sodium hydroxide solution (100 ml) and dichloromethane (50 ml). The aqueous layer was neutralised with 37% hydrochloric acid solution to pH7.2 and extracted with dichloromethane (4×50 ml). The combined organic extracts were dried over magnesium sulfate, filtered and the solvent removed in vacuo to give the product (12 g) as a cream solid.

Workup

  1. customThe methanol was removed in vacuo
  2. customthe residue partitioned between 10% sodium hydroxide solution (100 ml) and dichloromethane (50 ml)
  3. extractionextracted with dichloromethane (4×50 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-44e94dd0a92748fa913d6eefed5a8233
Source dataset
uspto-grants-2001_07
Patent number
US06262070B1

Reaction notes

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