4-Hydroxybenzyl Alcohol → HCID 178522925, compound

HRID 2289953Notes

Reaction equation

HRID 2289953 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[C:16]([F:25])[C:17](F)=[C:18]([F:23])[CH:19]=3)[N:14](COCC[Si](C)(C)C)[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[OH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[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]([O:42][C:39]2[CH:40]=[CH:41][C:36]([CH2:35][OH:34])=[CH:37][CH:38]=2)[C:16]=3[F:25])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18698511HCID 18698511, compound

Product 1

HCID 178522925HCID 178522925, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

N-((4-Chlorophenyl)methyl)-4-oxo-6,7,8-trifluoro-1-(2-(trimethylsilyl)ethoxy) methyl-3-quinolinecarboxamide (1.00 g) from Preparation No. 13 and 4-hydroxymethyl phenol (500 mg) are dissolved in DMF (20 mL). Sodium hydride (60% dispersion, 80 mg) is added and the mixture is heated to 140° C. for 1 h. The reaction mixture is allowed to cool to rt, is poured into sat. aq. ammonium chloride (100 mL), and is extracted with ethyl acetate (3×50 mL). The organic layer is washed with brine (10 mL), dried (MgSO4), and concentrated. The crude product is purified by column chromatography (heptane/ethyl acetate, 1/1; 1/5) followed by recrystallization to afford 145 mg of the title compound as a white solid.

Workup

  1. temperatureto cool to rt
  2. extractionis extracted with ethyl acetate (3×50 mL)
  3. washThe organic layer is washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product is purified by column chromatography (heptane/ethyl acetate, 1/1; 1/5)
  7. customfollowed by recrystallization

Sources & evidence

ORD record
ord-d0c2c6d497864450b7293eceac7cb597
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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