N-Methylaniline → 4-methoxy-N-methyl-N-phenylaniline

HRID 412767Notes

Reaction equation

HRID 412767 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:11]([CH3:10])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 7515N-MethylanilineHCID 121674-ChloroanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 37351784-methoxy-N-methyl-N-phenylanilineYield 93.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

According to the general procedure B, 4-chloroanisole (146 mg, 1.02 mmol) reacted with N-methylaniline (130 mg, 1.20 mmol) using 0.5 mol % Pd(OAc)2, 1 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (115 mg, 1.20 mmol) at 100° C. in toluene to give the title compound (203 mg, 93%) as a colorless oil: 1H-NMR (400 MHz, CDCl3):□ 7.24 (t, 2H, J=7.3 Hz), 7.13 (d, 2H, J=8.79 Hz), 6.93 (d, 2H, J=8.79 Hz), 6.82 (app.d, 3H, J=7.4 Hz), 3.85 (s, 3H), 3.29 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 156.23, 149.68, 142.15, 128.88, 126.21, 118.27, 115.62, 114.71, 55.46, 40.44. GC/MS(EI): m/z 213 (M+). Anal. Calcd for C14H15NO: C, 78.84; H, 7.09; N, 6.57. Found: C, 78.98; H, 7.12; N, 6.63.

Workup

  1. customat 100° C.

Sources & evidence

ORD record
ord-733ca697604e48e0868c5e8a374520c5
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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