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

HRID 264037Notes

Reaction equation

HRID 264037 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[C:10](O)(=O)[CH3:11].[C:14]([BH3-])#N.[Na+].Cl>CO.C1COCC1.CC(C)=O>[CH:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([CH3:11])[CH3:14]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 27594984-methoxy-N-(propan-2-yl)aniline

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-methoxy-phenylamine (1.24 g) in methanol (15 mL) at ambient temperature was added successively, glacial acetic acid (415 mg), acetone (669 mg), and 1M sodium cyanoborohydride in THF (12.7 mL). The reaction mixture was stirred overnight at room temperature. The pH was adjusted to 2 with 6N HCl and stirred for 30 minutes after which time the excess sodium cyanoborohydride was completely quenched. 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 oganic extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (1.42 g) as a yellow oil. 1H NMR (300 MHz, CDCl3): d 1.18(d, J=6.1 Hz, 6H), 2.92(br s, 1H), 3.55(m, 1H), 3.75(s, 3H), 6.57(d, J=9.1 Hz, 2H), 6.78(d, J=8.8 Hz, 2H) TLC (EtOAc/Hex (2:3)): Rf =0.72.

Workup

  1. customwas completely quenched
  2. extractionthe resultant solution extracted with diethyl ether (2×50 mL) and ethyl acetate (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a5afbadf6b44418a6a479723f702ab6
Source dataset
uspto-grants-1997_07
Patent number
US05646140

Reaction notes

Loading…