HCID 68513860, compound → HCID 59586785, compound

HRID 2091944Notes

Reaction equation

HRID 2091944 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([CH3:13])=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH3:23])=[O:21])=[CH:16][CH:15]=1)([CH3:3])[CH3:2]>CO.[Pd]>[NH2:10][C:8]1[C:7]([CH3:13])=[CH:6][C:5]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=1

Participants

4

Reactant 1

HCID 68513860HCID 68513860, compound

Product 1

HCID 59586785HCID 59586785, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2′-isopropyl-N,5′-dimethyl-4′-nitrobiphenyl-4-carboxamide is dissolved in methanol (20 mL). To this solution is added Pd/C (10%). The reaction mixture is degassed and purged with H2 for several times and then stirred under H2 (1 atm.) overnight. The mixture is filtered and concentrated to afford the title compound 4′-amino-2′-isopropyl-N,5′-dimethylbiphenyl-4-carboxamide as a white solid. 1H NMR (400 MHz, MeOD-d4) δ 7.87 (d, 2H, J=8.4 Hz), 7.35 (d, 2H, J=8.4 Hz), 7.31 (s, 1H), 7.14 (s, 1H), 3.00 (m, 1H), 2.95 (d, 3H), 2.36 (s, 3H), 1.15 (d, 6H, J=6.8 Hz); ESMS m/z 283.2 (M+H+).

Workup

  1. customThe reaction mixture is degassed
  2. custompurged with H2 for several times
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c93105e8250f4b7eb4233873635bafa5
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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