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

HRID 2183749Notes

Reaction equation

HRID 2183749 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-3122691d5a9c4fb5aa7846173d1a6d0b
Source dataset
uspto-grants-2005_05
Patent number
US06900232B2

Reaction notes

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