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

HRID 2106116Notes

Reaction equation

HRID 2106116 reaction equation
C([O-])=O.[NH4+].[CH2:5]([O:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21](=[O:23])[CH3:22])=[C:15]([N+:24]([O-])=O)[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(C)C=CC=CC=1>[Fe].O>[NH2:24][C:15]1[CH:14]=[C:13]([O:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:18]([O:19][CH3:20])=[CH:17][C:16]=1[C:21](=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 1140TolueneHCID 2723923Ammonium formateHCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

Product 1

HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanoneYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of iron powder (27 g, 0.48 g atoms), ammonium formate (31 g, 500 mmol), 1-(4-benzyloxy-5-methoxy-2-nitrophenyl)ethanone (36 g, 120 mmol), toluene (500 mL) and water (500 mL) was heated to reflux overnight. The mixture was filtered through celite and washed with ethyl acetate. The combined organic layers were washed with water and brine. The organic layer was dried over Na2SO4 and concentrated to afford 1-(2-amino-4-benzyloxy-5-methoxyphenyl)ethanone (29.3 g, 90%). 1H NMR (CDCl3): δ 7.41-7.30 (m, 5H), 7.13 (s, 1H), 6.16 (br s, 2H), 6.10 (s, 1H), 5.13 (s, 2H), 3.83 (s, 3H), 2.51 (s, 3H). LC/MS (M+H=272).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe mixture was filtered through celite
  4. washwashed with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a3a2b657bbbd46229408beeeac500f28
Source dataset
uspto-grants-2009_08
Patent number
US07579473B2

Reaction notes

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