HCID 15636997, compound → HCID 14822879, compound

HRID 1085478Notes

Reaction equation

HRID 1085478 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9](=[O:11])[NH:10][C:5]2=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1>CN(C=O)C.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:3]2[CH:4]=[C:5]3[NH:10][C:9](=[O:11])[NH:8][C:6]3=[N:7][C:2]=2[CH3:1])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 15636997HCID 15636997, compound

Product 1

HCID 14822879HCID 14822879, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Alternative preparation: To a solution of 21.40 g 1,3dihydro-5-methyl-6-(4-nitrophenyl)-2H-imidazo[4,5-b]pyridin-2-one in 1000 ml DMF was added 2.05 g palladium-on-carbon catalyst, and the mixture was hydrogenated in a Parr reactor at 50 psi and room temperature. After 90 min. the reaction was complete and the mixture was filtered and concentrated in vacuo. The residue was washed with water and dried in a vacuum oven to give an essentially quantitative yield of 6-(4-aminophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one in the free base form, m.p. above 300° C.

Workup

  1. customAlternative preparation
  2. customwas hydrogenated in a Parr reactor at 50 psi and room temperature
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with water
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-f7749d68ec624d1bb05377b8e899dc16
Source dataset
uspto-grants-1991_04
Patent number
US05010086

Reaction notes

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