Benzylamine → Diethyl 6-benzylaminopyridine-2,3-dicarboxylate

HRID 1898792Notes

Reaction equation

HRID 1898792 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:17]1[N:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:20]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:19][CH:18]=1>C(O)CC>[CH2:1]([NH:8][C:17]1[N:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:20]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 15451780Diethyl 6-chloropyridine-2,3-dicarboxylate

Product 1

HCID 15451773Diethyl 6-benzylaminopyridine-2,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

10.7 g (0.1 mol) of benzylamine and 10.1 g (0.1 mol) of triethylamine were added to a mixture of 25.8 g (0.1 mol) of diethyl 6-chloropyridine-2,3-dicarboxylate in 250 ml of propanol at 25° C. with stirring in the course of 10 minutes. After stirring under reflux for 12 hours, the reaction mixture was concentrated, the residue was taken up in methylene chloride and the solution was extracted with water. The organic phase was dried, filtered off with suction through neutral alumina and concentrated under reduced pressure. The residue was stirred in ether/pentane, filtered off with suction and dried, 23.3 g (71.1% of theory) of the title compound of m.p. 110°-114° C. being obtained.

Workup

  1. stirringAfter stirring
  2. temperatureunder reflux for 12 hours
  3. concentrationthe reaction mixture was concentrated
  4. extractionthe solution was extracted with water
  5. customThe organic phase was dried
  6. filtrationfiltered off with suction through neutral alumina
  7. concentrationconcentrated under reduced pressure
  8. stirringThe residue was stirred in ether/pentane
  9. filtrationfiltered off with suction
  10. customdried

Sources & evidence

ORD record
ord-d67ccef093ce4a38b7722319b3262294
Source dataset
uspto-grants-1996_11
Patent number
US05571774

Reaction notes

Loading…