Ethyl isonicotinate → 3-Pyridinemethanol

HRID 2293710Notes

Reaction equation

HRID 2293710 reaction equation
[C:1](OCC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:12](OCC)(=[O:19])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[OH:8][CH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[OH:19][CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 15291Ethyl isonicotinateHCID 69188Ethyl NicotinateHCID 21226445Aluminium lithium hydride

Product 2

HCID 75103-PyridinemethanolHCID 114724-Hydroxymethylpyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In Mosher, Harry S. et al., Journal Of American Chemical Society, 73 October (1951) pp. 4925-4927, 3-chloromethyl and 4-chloromethyl pyridinium hydrochloride was prepared by first reducing ethyl nicotinate and ethyl isonicotinate with lithium aluminum hydride in anhydrous ether to produce 3-hydroxymethyl pyridine and 4-hydroxymethyl pyridine respectively. The resulting liquid 3-hydroxymethyl pyridine was separated from the distillate by converting to the hydrochloride. The 3- and 4-hydroxymethyl pyridine hydrochloride were added to a substantial excess amount of thionyl chloride and then refluxed followed by the addition of benzene to precipitate out the 3- and 4-chloromethyl Pyridine hydrochloride, respectively. Although the resulting 3-chloromethyl pyridine hydrochloride compound appears to be very pure, it apparently exists as a fluffy dusty powder which is difficult to process on a large scale basis.

Sources & evidence

ORD record
ord-2ed974b790074316b98e9f4bbd94b8d1
Source dataset
uspto-grants-1997_11
Patent number
US05686619

Reaction notes

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