Hydrochloric Acid → (2,6-Dichloropyridin-4-yl)methanol

HRID 1590391Notes

Reaction equation

HRID 1590391 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([Cl:12])[CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C.Cl>ClCCl>[Cl:12][C:7]1[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[C:9]([Cl:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 948232,6-Dichloro-isonicotinic acid ethyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 2794840(2,6-Dichloropyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above ester was dissolved in dichloromethane (60 ml) and cooled to -20° under nitrogen. Diisobutylaluminium hydride (38 ml) was added dropwise. After 2 hours at 0°, dilute hydrochloric acid was carefully added and the mixture worked up in the usual manner to give 2,6-dichloro-4-hydroxymethylpyridine. NMR 1H: 7.64(2H,s), 4.98(2H,s).

Workup

  1. temperaturecooled to -20° under nitrogen

Sources & evidence

ORD record
ord-4c407586f22b41fbbaeed9084d58ba64
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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