3-Chlorotoluene → N,N-Dibutyl-3-methylaniline

HRID 412766

Reaction equation

HRID 412766 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:9]([N:13]([CH2:14][CH2:15][CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1)[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 79313-ChlorotolueneHCID 8148DibutylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 15332677N,N-Dibutyl-3-methylanilineYield 94.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

According to the general procedure B, 3-chlorotoluene (127 mg, 1.00 mmol) reacted with N,N-di-n-butylamine (155 mg, 1.20 mmol) using 0.5 mol % Pd(OAc)2, 1 mol % of ligand, and sodium tert-butoxide (115 mg, 1.20 mmol) at 100° C. for 27 h in toluene to give the title compound (208 mg, 94%) as a colorless oil: 1H-NMR (300 MHz, CDCl3): δ 7.15 (t, 1H, J=Hz), 6.53 (app.bd, 3H, J=3.3 Hz), 3.31 (t, 4H, J=7.5 Hz), 2.37 (s, 3H), 1.63 (m, 4H), 1.42 (m, 4H), 1.02 (t, 6H, J=7.2 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 148.27, 138.73, 129.02, 116.05, 112.39, 108.94, 50.74, 29.45, 22.02, 20.36, 14.01. GC/MS (EI): m/z 219 (M+). Anal. Calcd for C15H25N: C, 82.13; H, 11.49; N, 6.38. Found: C. 81.85; H, 11.57; N, 6.47.

Workup

  1. customat 100° C.
  2. customfor 27 h

Sources & evidence

ORD record
ord-e81ebb66b13045cf96105e3c97df2d6c
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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