Methanol → 3,4-Dihydro-2,7-naphthyridin-1(2H)-one

HRID 1844005Notes

Reaction equation

HRID 1844005 reaction equation
COC1C=CC(C[N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[C:9]1(=[O:18])[C:10]2[C:15](=[CH:14][CH:13]=[N:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1

Participants

7

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 112886342-(4-methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one

Product 1

HCID 111826883,4-Dihydro-2,7-naphthyridin-1(2H)-oneYield 72.53%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

2-(4-Methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one (I-65e: 700 mg, 2.6089 mmol) and p-toluene sulphonic acid (1.985 g, 10.436 mmol) in toluene (15 mL) were refluxed for 6 hours. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mass was neutralized with sodium carbonate solution, distilled off the solvent and added 10% methanol in CHCl3. The solid precipitated was filtered and distilled off the solvent to afford the crude product. Purification by column chromatography on silica gel (7% methanol in DCM) afforded 280 mg of the product (72.53% yield).

Workup

  1. distillationdistilled off the solvent
  2. additionadded 10% methanol in CHCl3
  3. customThe solid precipitated
  4. filtrationwas filtered
  5. distillationdistilled off the solvent
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (7% methanol in DCM)

Sources & evidence

ORD record
ord-d57edd0c178a4749ae18accdb5869c70
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…