Ammonium Hydroxide → (Z)-4,5-diamino-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one

HRID 1531159Notes

Reaction equation

HRID 1531159 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH3:21])/[C:5](=[O:14])[NH:6]2.[OH-].[NH4+].[H][H]>C1COCC1.[Pt]>[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH3:21])/[C:5](=[O:14])[NH:6]2

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 178418361HCID 178418361, compoundHCID 178433254HCID 178433254, compound

Product 1

HCID 178433244(Z)-4,5-diamino-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(Z)-4-azido-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one (150 mg, 0.48 mmol) (from Example 44 above) was suspended in THF (40 mL) at r.t. Ammonium hydroxide was added (0.15 mL), followed by a catalytic amount of poisoned platinum on carbon (50 mg, 5% Pt/C•½S) (Engelhard Ind.). The reaction mixture was hydrogenated in a Parr bomb under 50 psi of hydrogen for 16 h. The mixture was filtered through a cake of Celite®, and the cake was washed twice with THF. The crude material was purified by flash chromatography on Silica Gel (230-400 mesh, eluted with 1% MeOH/1% ET3N in THF) to afford (Z)-4,5-diamino-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one as a dark red solid. (Yield 52 mg, 42%).

Workup

  1. filtrationThe mixture was filtered through a cake of Celite®
  2. washthe cake was washed twice with THF
  3. customThe crude material was purified by flash chromatography on Silica Gel (230-400 mesh, eluted with 1% MeOH/1% ET3N in THF)

Sources & evidence

ORD record
ord-74e7aca5200144b2800646de045ba415
Source dataset
uspto-grants-2001_03
Patent number
US06197804B1

Reaction notes

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