Ethyl Acetate → 4,4'-Dimethoxybenzhydrylamine

HRID 1641884Notes

Reaction equation

HRID 1641884 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 (450 mL) and ethanol (90 mL). Ammonium acetate (3.00 g, 38.91 mmol) is added followed by the portion-wise addition of zinc dust (25.29 g, 389.1 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 for 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 for 4 hours
  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-4fecd04da9b04241b2d001e00d976dee
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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