Citric Acid → HCID 21834120, compound

HRID 1740871Notes

Reaction equation

HRID 1740871 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:36]C)=[C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=3)[NH:13][C:12](=[O:24])[C:11]=2[NH:25][CH2:26]N2C3C=CC=CC=3N=N2)[CH:9]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([OH:36])=[C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=3)[NH:13][C:12](=[O:24])[C:11]=2[NH:25][CH3:26])[CH:9]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 21834080HCID 21834080, compound

Product 1

HCID 21834120HCID 21834120, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride(151.2 mg, 4.0 mmol) was added to a solution of 4-(5-chloro-2-methoxyphenyl)-3-[[(1H-benzotriazol-1-yl)methyl]amino]-6-(trifluoromethyl)quinolin-2(1H)-one (1.0 g, 2.0 mmol) in absolute ethanol and heated to reflux for thirty minutes. The reaction was cooled, acidified with 10% citric acid, extracted with ethyl acetate, dried over magnesium sulfate, and concentrated. The resulting solid was then chromatographed on silica gel affording 4-(5-chloro-2-hydroxyphenyl)-3-(methylamino)-6-(trifluoromethyl)quinolin-2(1H)-one (200 mg, 26.1%).

Workup

  1. temperatureheated
  2. temperatureto reflux for thirty minutes
  3. temperatureThe reaction was cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting solid was then chromatographed on silica gel

Sources & evidence

ORD record
ord-a2dd07de04d14600aa4e781191743114
Source dataset
uspto-grants-1999_10
Patent number
US05972961

Reaction notes

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