Acetic Acid → 4-methoxy-N-(propan-2-yl)aniline

HRID 1599072Notes

Reaction equation

HRID 1599072 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(O)(=O)C.[CH3:14][C:15]([CH3:17])=O.C([BH3-])#N.[Na+].C1COCC1.Cl>CO>[CH:15]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([CH3:17])[CH3:14]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 180AcetoneHCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydride

Product 1

HCID 27594984-methoxy-N-(propan-2-yl)anilineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-methoxyphenylamine (1.24 g, 6.22 mmol) in methanol (15 mL) at ambient temperature was added successively, glacial acetic acid (415 mg, 6.91 mmol), acetone (669 mg, 11.5 mmol), and 1M sodium cyanoborohydride in THF (12.7 mL, 12.6 mmol). The reaction mixture was stirred overnight at room temperature. The pH was adjusted to 2 with 6N HCl and stirred for 30 minutes to quench excess sodium cyanoborohydride. The pH was then adjusted to 8.5 with 1N NaOH and the resultant solution extracted with diethyl ether (2×50 mL) and ethyl acetate (50 mL). The organic extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (1.42 g, 5.91 mmol) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 6.78(d, J=8.8 Hz, 2H), 6.57(d, J=9.1 Hz, 2H), 3.75(s, 3H), 3.55(m, 1H), 2.92(br s, 1H), 1.18(d, J=6.1 Hz, 6H); TLC (EtOAc/Hex (2:3)): Rf =0.72

Workup

  1. stirringstirred for 30 minutes
  2. customto quench excess sodium cyanoborohydride
  3. extractionthe resultant solution extracted with diethyl ether (2×50 mL) and ethyl acetate (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50b7fead31e3446cbfc03206c8998c9f
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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