Piperidine → Ethyl 2-hydroxy-1,8-naphthyridine-3-carboxylate

HRID 1961443Notes

Reaction equation

HRID 1961443 reaction equation
[NH2:1][C:2]1C(C=O)=[CH:6][CH:5]=[CH:4][N:3]=1.C([C:12]([CH2:19][CH3:20])([C:16]([O-:18])=O)[C:13]([O-:15])=[O:14])C.N1CCC[CH2:23][CH2:22]1>>[O:18]=[C:16]1[C:12]([C:13]([O:15][CH2:22][CH3:23])=[O:14])=[CH:19][C:20]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[NH:1]1

Participants

4

Reactant 3

HCID 8082PiperidineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 69515632,2-Diethylpropanedioate

Product 1

HCID 11564777Ethyl 2-hydroxy-1,8-naphthyridine-3-carboxylateYield 91%

Conditions

Temperature
120 °C

Procedure

2-Amino-3-pyridine carboxaldehyde (1.0 g, 8.19 mmol) was suspended in diethylmalonate (6.2 ml, 41.0 mmol) in a screw cap pressure tube. Piperidine (1.6 ml, 16.4 mmol) was added and the tube was sealed. The mixture was heated to 120° C. for 3.0 hours. The mixture was allowed to cool. The precipitate formed was filtered and washed with Et2O to yield 1.62 g (91%) of the title compound.

Workup

  1. customcap pressure tube
  2. customthe tube was sealed
  3. temperatureto cool
  4. customThe precipitate formed
  5. filtrationwas filtered
  6. washwashed with Et2O

Sources & evidence

ORD record
ord-28abf7985e8344c8a2782bd6678832b6
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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