Triphenylphosphine → 2-(4-methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one

HRID 1818910Notes

Reaction equation

HRID 1818910 reaction equation
O[CH2:2][CH2:3][C:4]1[C:9]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:11])=[CH:8][N:7]=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:12]2[CH2:2][CH2:3][C:4]3[C:9](=[CH:8][N:7]=[CH:6][CH:5]=3)[C:10]2=[O:11])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 668036304-(2-hydroxyethyl)-N-(4-methoxybenzyl)nicotinamide

Product 1

HCID 112886342-(4-methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-oneYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-hydroxy-ethyl)-N-(4-methoxy-benzyl)-nicotinamide (2.2 g, 7.683 mmol) and triphenylphosphine (4.03 g, 15.37 mmol) were dissolved in 50 mL of anhydrous THF. The mixture, while being stirred at 0° C. under the nitrogen atmosphere, dropwisely added with diethyl azocarboxylate (1.4 mL, 9.220 mmol) and stirred for about 1 hour at room temperature. The mixture was then concentrated under reduced pressure and a silica gel column chromatography (3% MeOH/MC) was performed on the resulting residue and obtained 1.88 g (91%) of 2-(4-methoxy-benzyl)-3,4-dihydro-2H-[2,7]naphtyridine-1-on in white solid.

Workup

  1. stirringstirred for about 1 hour at room temperature
  2. concentrationThe mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e9c0e1ac9fa4f8790d1b67610e97c34
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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