Hydrochloric Acid → 1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-5-((methoxyimino)methyl)-, 2-propenyl ester

HRID 484333

Reaction equation

HRID 484333 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH2:6][NH:7][CH2:8][CH2:9][CH:10]=1.Cl.O.Cl[C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15]>C1C=CC=CC=1.C(N(CC)CC)C>[CH3:1][O:2]/[N:3]=[CH:4]/[C:5]1[CH2:6][N:7]([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH2:8][CH2:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18052Allyl chloroformateHCID 1973131,2,5,6-Tetrahydropyridine-3-carboxaldehyde-O-methyloxime

Product 1

HCID 95887991(2H)-Pyridinecarboxylic acid, 3,6-dihydro-5-((methoxyimino)methyl)-, 2-propenyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde-O-methyloxime in 40 cm3 of benzene, 1.5 cm3 of triethylamine and 1.17 cm3 of 2-propenyl chloroformate are added. The mixture is agitated for 30 minutes at ambient temperature, then treated with 20 cm3 of 5% hydrochloric acid, then twice with 20 cm3 of water. The solvent is evaporated off, then the residue is distilled at 200° C. under 0.08 mbar. 2.25 g of the expected product is obtained.

Workup

  1. customThe solvent is evaporated off
  2. distillationthe residue is distilled at 200° C. under 0.08 mbar

Sources & evidence

ORD record
ord-25147420e1184deca8676bc11f13bfdc
Source dataset
uspto-grants-1993_07
Patent number
US05231107

Linked notes

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