Ethanol → HCID 11230072, compound

HRID 856596Notes

Reaction equation

HRID 856596 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[OH:12].C(O)C.O.[SH-].[Na+]>O1CCCC1>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[OH:12])=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 28015Sodium hydrosulfideHCID 11161395HCID 11161395, compound

Product 1

HCID 11230072HCID 11230072, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-chloro-4-nitrophenyl)(pyridin-2-yl)methanol (1 g) was dissolved in tetrahydrofuran (15 ml), ethanol (15 ml) and water (15 ml), and sodium hydrosulfide (3.3 g) was added to the mixture, and the mixture was refluxed for 30 minutes. After concentration, the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, to give (4-amino-2-chlorophenyl)(pyridin-2-yl)methanol (0.21 g) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. concentrationAfter concentration
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ee187ba4a7674c6293d85b7a53669713
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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