2-Chloroisonicotinic acid → (2-Chloropyridin-4-yl)methanol

HRID 1860389Notes

Reaction equation

HRID 1860389 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](O)=[O:9])[CH:5]=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 2369852-Chloroisonicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 7062237(2-Chloropyridin-4-yl)methanolYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-chloro-4-pyridinecarboxylic acid (2.5 g) in dry THF (100 ml) was added to a stirred solution of lithium aluminum hydride (20.6 ml, solution 1M in THF), kept at 23° and under a nitrogen atmosphere. The mixture was poured onto ice and extracted with EA (3×100 ml) and the organic extracts washed with brine, dried and concentrated in vacuo to give the title compound as a yellow solid (0.98 g).

Workup

  1. customkept at 23° and under a nitrogen atmosphere
  2. additionThe mixture was poured onto ice
  3. extractionextracted with EA (3×100 ml)
  4. washthe organic extracts washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd22ddae0c3c4b42959a82e27090ec59
Source dataset
uspto-grants-2003_03
Patent number
US06531466B2

Reaction notes

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