5-(Benzyloxy)-4-methoxy-2-nitrobenzamide → 2-Amino-5-(benzyloxy)-4-methoxybenzamide

HRID 61643Notes

Reaction equation

HRID 61643 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:20]([O-])=O)[CH:4]=1>C(O)(=O)C.CO.[Fe]>[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH2:20])[CH:4]=1

Participants

4

Reactant 1

HCID 593618645-(Benzyloxy)-4-methoxy-2-nitrobenzamide

Product 1

HCID 593619042-Amino-5-(benzyloxy)-4-methoxybenzamideYield 87.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 10129899Acetic acid methanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-methoxy-5-benzyloxy-2-nitrobenzamide (6.60 g, 21.9 mmol) and iron powder (8.14 g, 0.146 mol) in acetic acid/methanol (80 mL/80 mL) was heated at 85±5° C. for 1.5 h. The reaction mixture was allowed to cool to RT and the iron was removed by filtration, and volatiles were removed in vacuo. The residue was taken up in sat. sodium bicarbonate and the mixture was extracted with ethyl acetate (600 mL×3). The combined organic layers were washed with water (1×150 mL), brine (1×150 mL), dried (Na2SO4), filtered and concentrated in vacuo to give 4-methoxy-5-benzyloxy-2-aminobenzamide (5.2 g, 19.1 mmol, 87%). MS 273.2. (M+). HPLC retention time 4.585 min.

Workup

  1. temperatureto cool to RT
  2. customthe iron was removed by filtration, and volatiles
  3. customwere removed in vacuo
  4. extractionthe mixture was extracted with ethyl acetate (600 mL×3)
  5. washThe combined organic layers were washed with water (1×150 mL), brine (1×150 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57fdcff184644828abcbbea73c529a91
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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