Ethanol → 4-amino-N-propylbenzamide

HRID 1038800Notes

Reaction equation

HRID 1038800 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-])=O.CCO.[H][H]>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH3:13])=[O:9])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 3146644-Nitro-N-propylbenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 4283444-amino-N-propylbenzamideYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitro-N-propylbenzamide (3.31 g, 15.9 mmol) was dissolved in EtOAc (125 mL) and EtOH (125 mL) and passed through the H-Cube® at 1 mL/min equipped with a 10% Pd/C catcart (ThalesNano), at full hydrogen and temperature set to about 50° C. The solvent was stripped off and the solid was dried overnight in a vacuum oven set at about 50° C. to provide 4-amino-N-propylbenzamide (2.58 g, 91%): 1H NMR (DMSO-d6) δ 7.93 (t, J=5.48 Hz, 1H); 7.54 (d, J=8.57 Hz, 2H); 6.51 (d, J=8.67 Hz, 2H) 5.54 (br s, 2H) 3.13 (m, 2H) 1.47 (sextet, J=7.29 Hz, 2H) 0.85 (t, J=8.49 Hz, 3H).

Workup

  1. customset to about 50° C
  2. customthe solid was dried overnight in a vacuum oven
  3. customset at about 50° C.

Sources & evidence

ORD record
ord-94f1b246014d427dac517f8f647a5fbf
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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