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

HRID 1859067Notes

Reaction equation

HRID 1859067 reaction equation
[N:1]([C:4]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[C:9]2[C:5]=1/[C:6](=[CH:17]/[C:18]1[NH:19][CH:20]=[CH:21][CH:22]=1)/[C:7](=[O:16])[NH:8]2)=[N+]=[N-].[OH-].[NH4+].[H][H]>C1COCC1.[Pt]>[NH2:1][C:4]1[C:12]([NH2:13])=[CH:11][CH:10]=[C:9]2[C:5]=1/[C:6](=[CH:17]/[C:18]1[NH:19][CH:20]=[CH:21][CH:22]=1)/[C:7](=[O:16])[NH:8]2

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 21253446(Z)-4-azido-1,3-dihydro-5-nitro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 21253445(Z)-4,5-diamino-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(Z)-4-Azido-1,3-dihydro-5-nitro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (340 mg, 1.15 mmol)(from Example 11) was dissolved in THF at rt (30 mL). Ammonium hydroxide was added (0.36 ml), followed by a catalytic amount of poisoned platinum on carbon (5% Pt/C.1/2S, 50 mg) (Engelhard Industries). The reaction mixture was hydrogenated in a Parr bomb under 50 psi of hydrogen for 2.5 h. The mixture was filtered through a cake of Celite®, and the cake was washed twice with THF. The hydrogenation was repeated with a fresh batch of catalyst, solvent and ammonium hydroxide (50 psi, 2 h). After filtration through Celite®, the mixture was concentrated under reduced pressure. The crude material was purified by flash chromatography on Silica Gel (230-400 mesh, eluted with 75% ethyl acetate in hexanes) to yield (Z)-4,5-diamino-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 160 mg, 58%).

Workup

  1. filtrationThe mixture was filtered through a cake of Celite®
  2. washthe cake was washed twice with THF
  3. customwas repeated with a fresh batch of catalyst, solvent and ammonium hydroxide (50 psi, 2 h)
  4. filtrationAfter filtration through Celite®
  5. concentrationthe mixture was concentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography on Silica Gel (230-400 mesh, eluted with 75% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3c7553ea14d847449a955edc1d07aa36
Source dataset
uspto-grants-2000_11
Patent number
US06153634

Reaction notes

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