Ethanol → 1-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

HRID 2359000Notes

Reaction equation

HRID 2359000 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17](=[O:19])[CH3:18])=[C:11]([N+:20]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C>[Zn].O>[NH2:20][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([O:15][CH3:16])=[CH:13][C:12]=1[C:17](=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

Product 1

HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanoneYield 86%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-ethanone (11.94 g 39.6 mmol), ammonium chloride (13.48 g, 250 mmol), zinc powder (65.39 g, 1000 mmol), ethyl alcohol (720 ml) and water (70 ml) was refluxed until completion (5 hours). The mixture was filtered through celite and washed with hot ethyl alcohol. The filtrate was evaporated in vacuum. The residue was taken up in the mixture of chloroform (200 ml), water (200 ml) and the pH of this mixture was set to 8 by adding sodium hydroxide solution. The two layers were separated, the aqueous layer was extracted with chloroform (2×50 ml). The organic layers were combined, washed with water and over Na2SO4, and concentrated to give 9.25 product [α]. Yield 86%.

Workup

  1. temperaturewas refluxed until completion (5 hours)
  2. filtrationThe mixture was filtered through celite
  3. washwashed with hot ethyl alcohol
  4. customThe filtrate was evaporated in vacuum
  5. additionThe residue was taken up in the mixture of chloroform (200 ml), water (200 ml)
  6. additionby adding sodium hydroxide solution
  7. customThe two layers were separated
  8. extractionthe aqueous layer was extracted with chloroform (2×50 ml)
  9. washwashed with water and over Na2SO4
  10. concentrationconcentrated
  11. customto give 9.25 product [α]

Sources & evidence

ORD record
ord-31158c21c260495abd4b77b3e54f8f68
Source dataset
uspto-grants-2014_04
Patent number
US08685971B2

Reaction notes

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