4-Methoxybenzylamine → 3-(2-hydroxyethyl)-N-(4-methoxybenzyl)isonicotinamide

HRID 1844016Notes

Reaction equation

HRID 1844016 reaction equation
[C:1]1(=[O:11])[C:10]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[CH2:4][CH2:3][O:2]1.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1>C1COCC1>[OH:2][CH2:3][CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:1]([NH:19][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1)=[O:11]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 899638373,4-dihydro-1H-pyrano[4,3-c]pyridin-1-one

Product 1

HCID 899645143-(2-hydroxyethyl)-N-(4-methoxybenzyl)isonicotinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dihydro-1H-pyrano[4,3-c]pyridin-1-one (I-67e: 100 mg, (0.666 mmol) in THF (1 mL) was refluxed with p-methoxybenzylamine (0.9 mL, 6.66 mmol) to afford 220 mg of the crude product. LCMS: 95.54%, m/z=287.1 (M+1)

Sources & evidence

ORD record
ord-90d58b1865bc40d894a309ab5dac9c52
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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