Ammonia → C-(2,4-Dimethoxyphenyl)-C-(2-methoxyphenyl)methylamine

HRID 19714Notes

Reaction equation

HRID 19714 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[C:5](=[N:14]O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13].N.C([O-])(=O)C.[NH4+]>C(O)C.C(OCC)(=O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH:5]([NH2:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 517165Ammonium AcetateHCID 86611440HCID 86611440, compound

Product 1

HCID 43197268C-(2,4-Dimethoxyphenyl)-C-(2-methoxyphenyl)methylamine

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2′,4-Trimethoxybenzophenone oxime (6 g, 20.9 mmol) is dissolved in ethanol (30 ml) and concentrated aqueous ammonia (150 ml). Ammonium acetate (0.81 g, 10.45 mmol) is added, followed by zinc powder (6.79 g, 104 mmol). The reaction is heated to reflux for 4 hours, cooled to ambient temperature, diluted with ethyl acetate and filtered through a Celite™ filter. Evaporation affords the title compound. δH 3.78 (s 3H), 3.80 (s 3H), 3.82 (s 3H), 5.62 (s 3H), 6.40-6.50 (m 2H), 6.85-9.95 (m 2H), 7.10 (d J 8), 7.20-7.30 (m 2H)

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 4 hours
  3. filtrationfiltered through a Celite™
  4. filtrationfilter
  5. customEvaporation

Sources & evidence

ORD record
ord-d086c88d01994e01b7fbf7faf0ac7880
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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