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

HRID 562958Notes

Reaction equation

HRID 562958 reaction equation
C([O-])(=O)C.[NH4+].[CH2:6]([O:13][C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22](=[O:24])[CH3:23])=[C:16]([N+:25]([O-])=O)[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(C)C=CC=CC=1>[Fe].O>[NH2:25][C:16]1[CH:15]=[C:14]([O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:19]([O:20][CH3:21])=[CH:18][C:17]=1[C:22](=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

Product 1

HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A Mixture of iron powder (477 mmol, 27 g), ammonium acetate (500 mmol, 31 g), 1-(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-ethanone (120 mmol, 36 g), toluene (500 ml) and water (500 ml) was refluxed overnight until completion. The mixture was filtered through celite and washed with EtOAc. The organic layer was washed with water and Sat. NaCl, dried over Na2SO4, and concentrated to afford the product, 90%. 1H NMR (CDCl3): 7.408-7.298 (5H, m), 7.130 (1H, s), 6.155 (2H, br), 6.104 (1H, s), 5.134 (2H, s), 3.834 (3H, s), 2.507 (3H, s). LC/MS (M+1=272).

Workup

  1. temperaturewas refluxed overnight until completion
  2. filtrationThe mixture was filtered through celite
  3. washwashed with EtOAc
  4. washThe organic layer was washed with water and Sat. NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the product, 90%

Sources & evidence

ORD record
ord-6c76469836724c1da345d82e4d31e729
Source dataset
uspto-grants-2011_11
Patent number
US08067436B2

Reaction notes

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