Ammonia → 4-(Benzyloxy)-2-methylaniline

HRID 54424Notes

Reaction equation

HRID 54424 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].N>CO.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([CH3:18])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 2577204-(Benzyloxy)-2-methyl-1-nitrobenzene

Product 1

HCID 167730534-(Benzyloxy)-2-methylanilineYield 51%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 4-benzyloxy-2-methyl nitrobenzene (6.4 mmol, 1.5 g) and sodium hydrosulfite (16 mmol, 2.2 g) in 140 mL of MeOH/water (2:1) was refluxed for two hours. Upon cooling, the solution was poured into 500 mL of aqueous ammonia and the product extracted into CH2Cl2 (4×). The organic layer was washed with water, brine and dried over Na2SO4, filtered and concentrated to provide 4-benzyloxy-2-methylaniline (0.47 g, 51%) as a light brown oil. 1H NMR (300 MHz, CDCl3) δ:7.4 (m, 5 H), 6.76 (d, J=2.1 Hz, 1 H), 6.70 (dd, J=7.2, 2.1 Hz, 1 H), 6.61 (d, J=7.2 Hz, 1 H), 4.98 (s, 2 H), 2.15 (s, 3 H).

Workup

  1. temperatureUpon cooling
  2. extractionthe product extracted into CH2Cl2 (4×)
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed70e4a7a6fa4c1fa27c7de67ec8afcd
Source dataset
uspto-grants-1997_04
Patent number
US05622967

Reaction notes

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