Acetic Acid → N-isopropyl-2-phenoxyaniline

HRID 559833

Reaction equation

HRID 559833 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]([CH3:18])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:16]([NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:18])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 75899Benzenamine, 2-phenoxy-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 28545108N-isopropyl-2-phenoxyanilineYield 92.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-phenoxyaniline (0.93 g, 5.0 mmol) in dichloroethane (50 ml) was added anhydrous acetone (0.73 ml, 10.0 mmol) and acetic acid (0.1 ml, 2.0 mmol). The mixture was stirred for 30 min, and sodium triacetoxyborohydride (3.18 g, 15.0 mmol) was added in one portion. The reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched by slow addition of MeOH (10 ml) and concentrated under reduced pressure. The residue was poured into water (50 ml) and extracted with ethyl acetate (3×100 ml). Organic extracts were combined and washed with brine (2×100 ml) and dried (Na2SO4), concentrated under reduced pressure to give N-isopropyl-2-phenoxyaniline (1.05 g, 91%) as colorless oil.

Workup

  1. stirringThe reaction mixture was stirred overnight at ambient temperature
  2. customThe reaction mixture was quenched by slow addition of MeOH (10 ml)
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was poured into water (50 ml)
  5. extractionextracted with ethyl acetate (3×100 ml)
  6. washwashed with brine (2×100 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-499a0f79ac0c4383b3643b451568f71f
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Linked notes

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