2-Pyridinecarbonitrile, 4-methoxy-3,5-dimethyl- → 3,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine
Reaction equation
[CH3:1][C:2]1[C:3]([C:11]#N)=[N:4][CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].CC1C(CN)=NC=C(C)C=1[O:20]C.N([O-])=O.[Na+]>>[CH3:1][C:2]1[C:3]([CH2:11][OH:20])=[N:4][CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]Participants
4
Procedure
L. Pharma's U.S. Pat. No. 5,066,810 teaches a process to manufacture ##STR6## where X is OH or Cl by catalytic hydrogenation of 3,5-dimethyl-4-methoxy-2-cyanopyridine as depicted below ##STR7## in the presence of an inert diluent, the resulting 3,5-dimethyl-4-methoxy-2-aminomethylpyridine as depicted below ##STR8## which is then reacted with sodium nitrite in aqueous-acidic solution to give 3,5-dimethyl-4-methoxy-2-hydroxymethylpyridine and ultimately reacting the latter with thionyl chloride to give 3,5-dimethyl-4-methoxy-2-chloromethylpyridine.
Sources & evidence
- ORD record
- ord-69a41d1a03a149a981e8466e0954ab18
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121454
Reaction notes
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