Acetone → 4-methyl-N-(propan-2-yl)aniline

HRID 343138Notes

Reaction equation

HRID 343138 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:12])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH:10]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1)([CH3:12])[CH3:9]

Participants

6

Reactant 3

HCID 180AcetoneHCID 7813p-ToluidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 133317934-methyl-N-(propan-2-yl)anilineYield 97.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5.65 g (52.7 mmol) p-Toluidine and 3.21 g (55.4 mmol, 1.05 equiv) Acetone in 50 mL DCE is added 14.52 g (68.5 mmol, 1.3 equiv) Sodium triacetoxyborohydride and stirred 18 h at ambient temperature. The reaction mixture is diluted with DCM (200 mL), washed successively with H2O (75 mL), satd. NaHCO3 (75 mL), and brine (75 mL), dried (MgSO4), filtered and concentrated in vacuo to give 7.67 g (51.4 mmol) of Isopropyl-p-tolyl-amine as a pale amber oil: 1H NMR (CDCl3, 300 MHz) δ7.00 (d, 2H, J=8.3), 6.54 (d, 2H, J=8.4), 3.61 (m, 1H), 2.25 (s, 3H), 1.21 (d, 6H, J=6.3); TLC Rf =0.50 (EtOAc/Hexanes, 1:9).

Workup

  1. washwashed successively with H2O (75 mL)
  2. dry with materialNaHCO3 (75 mL), and brine (75 mL), dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cc257fcb8314c9e898db9c1a119c825
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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