Water → 3-chloro-2H-pyridine-1-carboxylic acid phenyl ester

HRID 1728187Notes

Reaction equation

HRID 1728187 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+].Cl[C:11]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].O>CO>[C:14]1([O:13][C:11]([N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH2:3]2)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 122873-ChloropyridineHCID 15891Phenyl chloroformateHCID 4311764Sodium borohydride

Product 1

HCID 575659013-chloro-2H-pyridine-1-carboxylic acid phenyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-chloro-pyridine (6.0 g, 53 mmol) in methanol (50 mL) was added NaBH4 (2.6 g, 69 mmol) at −78° C., following addition of phenyl chloroformate (8.3 g, 53 mmol) at same temperature. The mixture was stirred at r.t. for 0.5 h. Then water (200 mL) was added slowly into the solution. The precipitate was collected by filtration to give crude product (Yield: 8.2 g, 67%).

Workup

  1. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-16229c5392284f3aacb86bc065ad97e2
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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