2-Chlorotoluene → N-(o-tolyl)-N-methylaniline

HRID 412768Notes

Reaction equation

HRID 412768 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:3]1([CH3:8])[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:10]([CH3:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 72382-ChlorotolueneHCID 7515N-MethylanilineHCID 23676156Sodium t-butoxide

Product 1

HCID 14692921N-(o-tolyl)-N-methylanilineYield 89.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

According to the general procedure B, 2-chlorotoluene (129 mg, 1.02 mmol) reacted with N-methylaniline (133 mg, 1.20 mmol) using 0.5 mol % Pd(OAc)2, 1 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (120 mg, 1.25 mmol) in toluene at 100° C. to give the title compound (180 mg, 89%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 7.37-7.21 (m, 6H), 6.78 (t, 1H, J=7.25 Hz), 6.61 (d, 2H, J=7.86 Hz), 3.30 (s, 3H), 2.22 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 149.08, 146.74, 136.80, 131.32, 128.93, 128.30, 127.46, 126.38, 116.72, 112.76, 39.00, 17.83. GC/MS(EI): m/z 197 (M+). Anal. Calcd for C14H15N: C, 85.24; H, 7.66; N, 7.10. Found: C, 85.09; H, 7.71; N, 7.24.

Workup

  1. customat 100° C.

Sources & evidence

ORD record
ord-4dcaab1effb246bc9371daacc1184955
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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