1-(1-Chloroethyl) 4-ethyl 3,6-dihydro-1,4(2H)-pyridinedicarboxylate → Ethyl 1,2,3,6-tetrahydropyridine-4-carboxylate

HRID 1394065Notes

Reaction equation

HRID 1394065 reaction equation
[N:1]1(C(OC(Cl)C)=O)[CH2:6][CH:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1>CO>[NH:1]1[CH2:2][CH:3]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 692236561-(1-Chloroethyl) 4-ethyl 3,6-dihydro-1,4(2H)-pyridinedicarboxylate

Product 1

HCID 13859979Ethyl 1,2,3,6-tetrahydropyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(1-Chloroethyl) 4-ethyl 3,6-dihydro-1,4(2H)-pyridinedicarboxylate (61.8 g, 236 mmol) in methanol (500 mL) was heated at reflux for 30 minutes. The mixture was allowed to cool to room temperature and concentrated to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 6.86 (m, 1H), 4.22 (q, 2H), 3.85 (m, 2H), 3.34 (m, 2H), 2.75 (m, 2H), 1.30 (t, 3H).

Workup

  1. temperatureat reflux for 30 minutes
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-cb3e94fee45f473cb30276afdb6ad07a
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

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