L-Proline → 1,8-Naphthyridine, 2-methyl-

HRID 1815985Notes

Reaction equation

HRID 1815985 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][N:3]=1.N1CC[CH2:15][C@H:11]1[C:12](O)=O>CC(C)=O>[CH3:15][C:11]1[CH:12]=[CH:8][C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[N:1]=1

Participants

4

Reactant 2

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 740731,8-Naphthyridine, 2-methyl-Yield 641.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-amino-3-pyridinecarboxaldehyde (from step c, 24.57 g) in acetone (750 mL) was added proline (2.3 g, 20 mmole), then the mixture was heated to reflux. After 48 hr the mixture was cooled to RT, filtered, and concentrated. Flash column chromatography on silica gel (35% acetone/hexanes) gave the title compound (18.5 g, 64% over 3 steps) as an orangish-yellow solid: 1H NMR (300 MHz, CDCl3) δ 9.07 (m, 1 H), 8.10 (m, 2H), 7.40 (m, 2H), 2.80 (s, 3H); MS (ES) m/e 145 (M+H)+.

Workup

  1. temperaturethe mixture was heated to reflux
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9069fc2a22764831a9594691d8cef594
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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