Acetone → 1,8-Naphthyridine, 2-methyl-

HRID 497548Notes

Reaction equation

HRID 497548 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:10][C:11]([CH3:13])=O>C(O)C>[CH3:13][C:11]1[CH:10]=[CH:8][C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[N:1]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 740731,8-Naphthyridine, 2-methyl-Yield 70.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound was prepared according to the procedure as described by E. M. Hawes and D. G. Wibberley, J. Chem. Soc. (C), 1966, 315. To a solution of 2-amino-3-pyridinecarboxaldehyde (2 g, 16 mmol) in ethanol 3 ml) was added acetone (1.9 g, 32 mmol) and peperidine (0.34 g, 4 mmol) and the reaction mixture was refluxed 24 hours. Reaction mixture was cooled to room temperature then concentrated in vacuum. Ether was added to concentrated residue. Solid was filtered and dried to give 1.62 g (69%) yellow solid. NMR (CD3OD) δ 2.76 (s, 3H), 7.52-7.58 (m, 2H), 8.30 (d, 2H, J=8.33 Hz), 8.36-8.39 (m, 1H), 8.39-8.99 (m, 1H).

Workup

  1. customThe compound was prepared
  2. temperaturethe reaction mixture was refluxed 24 hours
  3. customReaction mixture
  4. concentrationthen concentrated in vacuum
  5. additionEther was added to concentrated residue
  6. filtrationSolid was filtered
  7. customdried

Sources & evidence

ORD record
ord-ba50da11a1094ed395eec0098da3c52d
Source dataset
uspto-grants-2005_09
Patent number
US06949578B2

Reaction notes

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