N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamine → N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide

HRID 2393442Notes

Reaction equation

HRID 2393442 reaction equation
CN(C)[CH:3]=[CH:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][N:8]=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=1.[H][H]>C(O)C.[Pt]=O>[C:15]([NH:14][C:7]1[CH:6]=[C:5]2[CH:4]=[CH:3][NH:11][C:10]2=[CH:9][N:8]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 53811652N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamineHCID 178418361HCID 178418361, compound

Product 1

HCID 18975304N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamideYield 33.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamine (6 g, 24 mmol) was hydrogenated over platinum oxide (0.5 g) in ethanol (120 mL) at 35 psi of hydrogen for 15 min. The catalyst was removed by filtration and the solvent evaporated in vacuo. The residue was chromatographed on silica eluting with a gradient of 5 to 10% MeOH in DCM to afford a purple solid. This was triturated with ether and the precipitate collected by filtration to give the title compound (1.4 g, 33%) as a beige solid. mp 220° C. (dec.). 1H NMR (360 MHz, d6 -DMSO) δ 2.07 (3H, s), 6.45 (1H, s), 7.55-7.57 (1H, m), 8.21 (1H, s), 8.46 (1H, s), 10.16 (1H, br s) and 11.42 (1H, br s).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated in vacuo
  3. customThe residue was chromatographed on silica eluting with a gradient of 5 to 10% MeOH in DCM
  4. customto afford a purple solid
  5. customThis was triturated with ether
  6. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-928529796528427aa2e02af5cdff0ed9
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

Loading…