N-Methyl-4-anisidine → 1-Isoquinolinamine, N-(4-methoxyphenyl)-N-methyl-

HRID 1876101Notes

Reaction equation

HRID 1876101 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[CH:16][CH:15]=1>>[C:2]1([N:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 22250N-Methyl-4-anisidineHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 113000521-Isoquinolinamine, N-(4-methoxyphenyl)-N-methyl-Yield 57%

Conditions

Temperature
140 °C

Procedure

A mixture of 1-chloroisoquinoline (50 mg, 0.31 mmol) and (4-methoxy-phenyl)-methyl amine (300 mg, 2.2 mmol) was heated in a sealed tube at 140° C. overnight. The crude product was purified by chromatography (5-6% ethyl acetate/hexanes) on silica gel to give the title compound (46 mg, 0.17 mmol, 57%). 1H NMR (CDCl3): 8.22 (d, 1H, 5.7), 7.68 (d, 1H, J=8.1), 7.62 (d, 1H, J=8.7), 7.47 (ddd, 1H, J=0.9, 6.9, 8.1), 7.24 (d, 1H, J=6.0), 7.19 (ddd, 1H, J=1.5, 6.9, 8.7), 6.94 (m, 2H), 6.79 (m, 2H), 3.76 (s, 3H), 3.52 (s, 3H).

Workup

  1. customThe crude product was purified by chromatography (5-6% ethyl acetate/hexanes) on silica gel

Sources & evidence

ORD record
ord-7d191d93287e407f8a465f760f1f5936
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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