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

HRID 2277401Notes

Reaction equation

HRID 2277401 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.C([O-])=O.[NH4+]>C1(C)C=CC=CC=1.O.CCOC(C)=O.[Fe]>[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 2

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

Product 1

HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanoneYield 99%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolventHCID 22272177Toluene waterSolvent

Conditions

Temperature
103 °C

Procedure

A suspension of 1-(4-Benzyloxy-5-methoxy-2-nitrophenyl)ethanone (36.00 g, 120 mmol), iron powder (26.80 g, 480 mmol) and HCOONH4 (31.53 g, 500 mmol) in a mixture of toluene/water (500 mL/500 mL) was stirred at 103° C. overnight. The mixture was cooled to room temperature, diluted with EtOAc (500 mL), stirred at room temperature for 3 hours, and filtered through a celite pad. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (32.1 g, 99%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringstirred at room temperature for 3 hours
  3. filtrationfiltered through a celite pad
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fff5645a123a473d8c97ed36eb711db3
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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