Triethylamine → 1-(4-nitrophenyloxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime

HRID 484334

Reaction equation

HRID 484334 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH3:14][O:15][N:16]=[CH:17][C:18]1[CH2:19][NH:20][CH2:21][CH2:22][CH:23]=1.C(N(CC)CC)C>ClCCl>[CH3:14][O:15][N:16]=[CH:17][C:18]1[CH2:19][N:20]([C:2]([O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)=[O:3])[CH2:21][CH2:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 1973131,2,5,6-Tetrahydropyridine-3-carboxaldehyde-O-methyloxime

Product 1

HCID 30728631-(4-nitrophenyloxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloximeYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 97% 4-nitrophenyl chloroformate (1.5 g, 7.22 mmoles) in dichloromethane (15 mL) was added at 0° C. to a stirred solution of 1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime (0.92 g, 6.6 mmoles) and triethylamine (0.92 mL, 6.6 mmoles) in dichloromethane (20 mL). The reaction mixture was then stirred at room temperature for 20 minutes, the solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4) and evaporated. The solid was recrystallized from benzene-cyclohexane to give 1.9 g (95%) of the desired product with mp 109°-110° C.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated
  5. customThe solid was recrystallized from benzene-cyclohexane

Sources & evidence

ORD record
ord-fd4c77fa32594158be7a2ba968f393e8
Source dataset
uspto-grants-1993_07
Patent number
US05231107

Linked notes

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