Acetone → 1-[3-(Dimethylamino)phenyl]propan-2-one

HRID 595366Notes

Reaction equation

HRID 595366 reaction equation
[CH3:1][N:2]([C:4]1[CH:5]=[C:6](Cl)[CH:7]=[CH:8][CH:9]=1)[CH3:3].P.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:18][C:19]([CH3:21])=[O:20]>C(Cl)C=CC1C=CC=CC=1.[Pd]>[CH3:1][N:2]([C:4]1[CH:5]=[C:6]([CH2:18][C:19](=[O:20])[CH3:21])[CH:7]=[CH:8][CH:9]=1)[CH3:3]

Participants

6

Reactant 4

HCID 180AcetoneHCID 10796Cesium carbonateHCID 23285N,N-Dimethyl-3-chloroanilineHCID 24404Phosphine

Product 1

HCID 571738381-[3-(Dimethylamino)phenyl]propan-2-oneYield 69%

Reagents, catalysts & solvents 1

HCID 131734589Palladium cinnamyl chlorideCatalyst

Procedure

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are 3-(N,N-Dimethylamino)phenyl chloride (156.0 mg, 0.99 mmol), palladium cinnamyl chloride (7.8 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)henyldicyclohexyl)phosphine (24.6 mg, 0.060 mmol), Cs2CO3 (653.2 mg, 2.0 mmol) in 4.0 mL acetone at 90° C. for 12 h. 1-[3′-(N, N-Dimethylamino)phenyl]-2-propanone (122.2 mg) was obtained with a yield of 69% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.21 (t, J=7.8 Hz, 1H, ArH), 6.69-6.62 (m, 1H, ArH), 6.61-6.53 (m, 2H, ArH), 3.64 (s, 2H, CH2), 2.95 (s, 6H, N(CH3)2), 2.15 (s, 3H, COCH3); 13C NMR (75 MHz, CDCl3) δ 207.0, 150.7, 135.0, 129.3, 117.4, 113.1, 111.1, 51.6, 40.4, 28.9; IR (neat) v (cm−1) 3033, 2916, 2805, 1712, 1603, 1580, 1504, 1440, 1354, 1271, 1229, 1178, 1156, 1062; MS (70 eV, EI) m/z (%): 178 (M++1, 9.69), 177 (M+, 73.88), 134 (100).

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 90° C.
  3. customfor 12 h

Sources & evidence

ORD record
ord-d9ed284ca9d448bcb4efa2630d77ea70
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Reaction notes

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