HCID 136386881, compound → HCID 136386882, compound

HRID 2421496Notes

Reaction equation

HRID 2421496 reaction equation
[N+:1]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3[C:14](=[O:27])[NH:15][CH:16]=[CH:17][C:18]=3[NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.O1CCCC1.[Pt]=O>[NH2:1][C:4]1[C:12]2[N:11]=[C:10]([C:13]3[C:14](=[O:27])[NH:15][CH:16]=[CH:17][C:18]=3[NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 136386881HCID 136386881, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136386882HCID 136386882, compoundYield 113%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)Catalyst2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Platinum oxide (0.146 g, 0.65 mmol) was added to a stirred solution of 3-(4-nitro-1H-benzoimidazol-2-yl)-4-[(pyridin-2-ylmethyl)-amino]-1H-pyridin-2-one in methanol (12 ml) and tetrahydrofuran (12 ml). The reaction was purged with nitrogen three times and the atmosphere replaced with hydrogen and the reaction stirred at room temperature. After 72 hours the reaction was recharged with platinum oxide (0.146 g, 0.65 mmol) and hydrogen and stirred for a further 24 hours. The reaction was filtered through Celite and the filter cake washed with tetrahydrofuran and methanol. The solvent was concentrated under reduced pressure to give the desired crude aniline (0.610 g, 113%), which was used without further purification.

Workup

  1. customThe reaction was purged with nitrogen three times
  2. stirringstirred for a further 24 hours
  3. filtrationThe reaction was filtered through Celite
  4. washthe filter cake washed with tetrahydrofuran and methanol
  5. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2f44b2b90d1a46e491a560cf31e84821
Source dataset
uspto-grants-2011_06
Patent number
US07956190B2

Reaction notes

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