Isopropanol → HCID 178458751, compound

HRID 2289956Notes

Reaction equation

HRID 2289956 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([F:23])=[C:17](F)[C:16]=3[F:25])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28][CH:29]([OH:31])[CH3:30].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([F:23])=[C:17]([O:31][CH:29]([CH3:30])[CH3:28])[C:16]=3[F:25])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 178522923HCID 178522923, compound

Product 1

HCID 178458751HCID 178458751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-((4-Chlorophenyl)methyl)-4-hydroxy-6,7,8-trifluoro-3-quinolinecarboxamide (500 mg) from Example No. 15 and sodium hydride (60% dispersion, 109 mg) are dissolved in DMF (10 mL) and to the mixture is added 2-propanol (115 μL). After being heated for 1 h, additional sodium hydride (50 mg) is added, and the mixture is heated for an additional 1 h. The reaction mixture is allowed to cool to rt, poured into sat. aq. ammonium chloride (25 mL), and is filtered. The crude product is purified by column chromatography (dichloromethane/methanol, 100/1) to afford 62 mg of the title compound as a white solid.

Workup

  1. temperatureAfter being heated for 1 h
  2. temperaturethe mixture is heated for an additional 1 h
  3. filtrationis filtered
  4. customThe crude product is purified by column chromatography (dichloromethane/methanol, 100/1)

Sources & evidence

ORD record
ord-a11e60eaae2b48118812585621c29d35
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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