Ammonium formate → 4-Amino-3-ethoxybenzamide

HRID 450527Notes

Reaction equation

HRID 450527 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:7]([NH2:9])=[O:8])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[NH2:13][C:12]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][C:4]=1[O:3][CH2:1][CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 672173043-Ethoxy-4-nitrobenzamide

Product 1

HCID 633567064-Amino-3-ethoxybenzamideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (5%, 0.510 g) was added into a solution of 3-ethoxy-4-nitro-benzamide (1.694 g, 8.06 mmol) and ammonium formate (2.17 g, 34.4 mmol) in MeOH (25 mL) at ambient temperature. The solution was stirred for 1 hour, filtered through Celite and washed with MeOH. The filtrate was concentrated in vacuo and triturated from diethyl ether to yield white solid (1.45 g, 100%).

Workup

  1. filtrationfiltered through Celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customtriturated from diethyl ether

Sources & evidence

ORD record
ord-797f3a9a25384f62a5fd74f9d535e273
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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