2-Chlorotoluene → HCID 12135563, compound

HRID 412774Notes

Reaction equation

HRID 412774 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH2:9]([NH2:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:9]([NH:15][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 72382-ChlorotolueneHCID 8102HexylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 12135563HCID 12135563, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

According to the general procedure B, 2-chlorotoluene (73 mg, 0.58 mmol) reacted with n-hexylamine (80 μl, 0.61 mmol) using 1 mol % of Pd(dba)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (59 mg, 0.60 mmol) in toluene at 70° C. for 8 h to give the title compound (102 mg, 92%) as a colorless oil: 1H-NMR (300 MHz, CDCl3): δ 7.20 (t, 1H, J=7.5 and 7.8 Hz), 7.12 (d, 1H, J=7.2 Hz), 6.70 (dd, 2H, J=7.5 Hz), 3.51 (bs, 1H), 3.22 (t, 2H, J=7.2 Hz), 2.21 (s, 3H), 1.74 (m, 2H), 1.48 (m, 2H), 1.41 (m, 2H). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.35, 129.94, 127.08, 121.60, 116.53, 109.52, 43.91, 31.64, 29.54, 26.90, 22.62, 17.43, 14.03. GC/MS(EI): m/z 191 (M+), 121. Anal. Calcd for C13H21N: C, 81.62; H, 11.06; N, 7.32. Found: C, 81.52; H, 11.09; N, 7.37.

Workup

  1. customat 70° C.
  2. customfor 8 h

Sources & evidence

ORD record
ord-6d0c760d825a4a978f3e5ba8ad8b0f51
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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