Phosphorus oxychloride → (6-Chloropyridin-3-yl)methanol

HRID 1089437Notes

Reaction equation

HRID 1089437 reaction equation
O[C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12].P(Cl)(Cl)(Cl)=O.[BH4-].[Na+]>O>[Cl:12][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 4311764Sodium borohydrideHCID 178418479HCID 178418479, compound

Product 1

HCID 177161(6-Chloropyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

69.5 g (0.5 mol) of 6-hydroxynicotinic acid are introduced into a mixture of 200 g (1 mol) of phosphorus pentachloride and 233 g (1.5 mol) of phosphorus oxychloride at room temperature, the mixture is stirred at 95° C. for 5 hours and excess phosphorus chlorides are then removed in vacuo. The crystalline residue is introduced into a solution of 75 g (1.98 mol) of sodium borohydride in 1,000 ml of water, the temperature being maintained at 30° C. at most. The mixture is then stirred at room temperature until the completion of gas evolution and is filtered with suction from solid material, and the filtrate is extracted using ether.

Workup

  1. customexcess phosphorus chlorides are then removed in vacuo
  2. temperaturethe temperature being maintained at 30° C. at most
  3. stirringThe mixture is then stirred at room temperature until the completion of gas evolution
  4. filtrationis filtered with suction from solid material
  5. extractionthe filtrate is extracted

Sources & evidence

ORD record
ord-9b318b68d7934b408c68e02d89066c34
Source dataset
uspto-grants-1990_10
Patent number
US04966902

Reaction notes

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