2-Nitrobenzene-1,3-dicarboxamide → 2-Aminobenzene-1,3-dicarboxamide

HRID 59951

Reaction equation

HRID 59951 reaction equation
[N+:1]([C:4]1[C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])([O-])=O>CN(C=O)C.[Pd]>[NH2:1][C:4]1[C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7]

Participants

4

Reactant 1

HCID 141474892-Nitrobenzene-1,3-dicarboxamide

Product 1

HCID 102413842-Aminobenzene-1,3-dicarboxamideYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-nitro-isophthalamide (6 g, 0.028 mol) and Pd/C (0.6 g) in DMF (100 mL) was hydrogenated at RT under hydrogen bladder pressure for 16 h. The reaction mixture was filtered through celite bed, washed with DMF and filtrate was evaporated under vacuum to afford the title compound as a brown solid (yield 78%). LC-MS [178 (M−H)], 1H NMR (400 MHz, DMSO-d6): δ 7.97 (s, 2H), 7.84 (brs, 2H), 7.65 (d, J=7.76 Hz, 2H), 7.22 (brs, 2H), 6.49 (t, J=7.76 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through celite bed
  2. washwashed with DMF and filtrate
  3. customwas evaporated under vacuum

Sources & evidence

ORD record
ord-4b4189981cfc4f6d8129804551993580
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Linked notes

Loading…