Diphenyl-(5-nitro-2-pyridyl)acetamide → HCID 10902759, compound

HRID 736364Notes

Reaction equation

HRID 736364 reaction equation
[C:1]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][N:12]=2)[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCO.[Pt](=O)=O>[C:20]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][N:12]=2)[C:8]([NH2:10])=[O:9])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 11045860Diphenyl-(5-nitro-2-pyridyl)acetamide

Product 1

HCID 10902759HCID 10902759, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8.86 g of diphenyl-(5-nitro-2-pyridyl)acetamide (26.5 mmol) in 50% EtOH/glacial AcOH with 100 mg platinum (IV) oxide was shaken on a Parr hydrogenator (30 psi H2) for 3 hr. The mixture was filtered through a bed of Celite, then the ethanol was evaporated under reduced pressure. The mixture was then basified with K2CO3 and extracted with EtOAc (4×), dried (MgSO4), filtered through Celite again and evaporated. The remaining solid was recrystallized from hexane/EtOAc/MeOH to furnish the title compound (7.9 g, 98%) as a tan crystal. mp 215-20° C. 1H NMR (CDCl3; 300 MHz) δ 3.85 (2H, bs, NH), 5.88 (1H, bs, CONH), 6.54 (1H, d, J=8.4 Hz), 6.84 (1H, dd, J=3 and 8.7 Hz), 7.01 - 7.06 (4H, m), 7.24-7.32 (6H, m), 8.11 (1H, d, J=2.4 Hz, H-6), 9.57 (1H, bs, CONH). Elemental analysis calculated for C19H17N3O 0.25 H2O: C, 74.15; H, 5.69; N, 13.67. Found: C, 74.06; N, 5.69; H, 13.78.

Workup

  1. filtrationThe mixture was filtered through a bed of Celite
  2. customthe ethanol was evaporated under reduced pressure
  3. extractionextracted with EtOAc (4×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through Celite again
  6. customevaporated
  7. customThe remaining solid was recrystallized from hexane/EtOAc/MeOH

Sources & evidence

ORD record
ord-c3449db4fe29431388f428d1091ba240
Source dataset
uspto-grants-2009_09
Patent number
US07595331B2

Reaction notes

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