Triphenylphosphine → 2-(4-Methoxybenzyl)-3,4-dihydro-2,6-naphthyridin-1(2H)-one

HRID 1844017Notes

Reaction equation

HRID 1844017 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:21]=[N:20][CH:19]=[CH:18][C:5]=1[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:7].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:8]2[CH2:2][CH2:3][C:4]3[C:5](=[CH:18][CH:19]=[N:20][CH:21]=3)[C:6]2=[O:7])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 899645143-(2-hydroxyethyl)-N-(4-methoxybenzyl)isonicotinamide

Product 1

HCID 735546032-(4-Methoxybenzyl)-3,4-dihydro-2,6-naphthyridin-1(2H)-oneYield 145.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Hydroxyethyl)-N-(4-methoxybenzyl)isonicotinamide (220 mg, 0.769 mmol) was reacted with PPh3 (403 mg, 1.538 mmol), DEAD (0.15 mL, 0.922 mmol) and THF (10 mL) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 300 mg of the product. LCMS: 66.95%, m/z=269.0 (M+1)

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

Sources & evidence

ORD record
ord-a1b3bcd25d6c4edebe54b0dff97e0005
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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