Hydrazine hydrate (1:1) → 3-[2-(4-Aminophenyl)ethyl]-8-benzyl-1-propylxanthine

HRID 29863Notes

Reaction equation

HRID 29863 reaction equation
[CH2:1]([C:8]1[NH:16][C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[H][H]>[Pd]>[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][CH2:22][N:11]2[C:10]3[N:9]=[C:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[NH:16][C:15]=3[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12]2=[O:21])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 103655718-Benzyl-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthineHCID 178418361HCID 178418361, compound

Product 1

HCID 99091463-[2-(4-Aminophenyl)ethyl]-8-benzyl-1-propylxanthine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

By methods well known in the art, 8-benzyl-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine (9) is reduced with hydrazine hydrate or hydrogen gas in the presence of a palladium catalyst to yield 3-[2-(4-aminophenyl)ethyl]-8-benzyl-1-propylxanthine.

Sources & evidence

ORD record
ord-b8e5a392a1284771a205938f5e5be545
Source dataset
uspto-grants-2008_09
Patent number
US07423041B2

Reaction notes

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