Ethyl Acetate → 4,4'-Dimethoxybenzhydrylamine

HRID 1696966Notes

Reaction equation

HRID 1696966 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[N:10]O)=[CH:5][CH:4]=1.C([O-])(=O)C.[NH4+].C(OCC)(=O)C>N.C(O)C.[Zn]>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH:9]([NH2:10])[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 289718n-Hydroxy-1,1-bis(4-methoxyphenyl)methanimineHCID 517165Ammonium Acetate

Product 1

HCID 3500424,4'-Dimethoxybenzhydrylamine

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Bis-(4-methoxy-phenyl)-methanone oxime (20 g, 77.82 mmol) is suspended in ammonia 0.880(450 ml) and ethanol (90 ml). Ammonium acetate (3.00 g, 38.91 mmol) is added followed by the portionwise addition of zinc dust (25.29 g, 389.10 mmol). Once the addition is complete the reaction mixture is slowly heated to 50° C. When the effervescence has ceased the reaction mixture is refluxed. The reaction is shown to be complete by TLC after 4 hours. The reaction mixture is allowed to cool and ethyl acetate is added (250 ml). The reaction mixture is filtered through Celite™ and the phases are separated. The organic layer dried is over MgSO4, filtered and the solvent removed in vacuo to give the title compound. 1H nmr (CDCl3, 400 MHz); 7.25 (d, 4H), 6.80(d, 4H), 5.10(s, 1H), 3.75(s, 6H).

Workup

  1. additionOnce the addition
  2. temperatureis refluxed
  3. temperatureto cool
  4. filtrationThe reaction mixture is filtered through Celite™
  5. customthe phases are separated
  6. customThe organic layer dried
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-eac1ee1928fb4583b20be929a2cc2152
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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