N-(3-(2-(Dimethylamino)pyrimid-5-yl)phenyl)-2-nitro-4-(1-pyrrolyl)aniline → N-(3-(2-(Dimethylamino)pyrimid-5-yl)phenyl)-2-amino-4-(1-pyrrolyl)aniline

HRID 1075460Notes

Reaction equation

HRID 1075460 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[CH:23]4)=[CH:18][C:17]=3[N+:27]([O-])=O)[CH:12]=[CH:13][CH:14]=2)=[CH:5][N:4]=1.[H][H]>[Pd].C(O)C>[CH3:1][N:2]([CH3:30])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[CH:23]4)=[CH:18][C:17]=3[NH2:27])[CH:12]=[CH:13][CH:14]=2)=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 53636071N-(3-(2-(Dimethylamino)pyrimid-5-yl)phenyl)-2-nitro-4-(1-pyrrolyl)anilineHCID 178418361HCID 178418361, compound

Product 1

HCID 54357107N-(3-(2-(Dimethylamino)pyrimid-5-yl)phenyl)-2-amino-4-(1-pyrrolyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 3f (0.2g, 0.5mmol) in abs. ethanol is added palladium catalyst (5% Pd on activated carbon) and the mixture is hydrogenated at ambient pressure until the hydrogen uptake has ceased. The mixture is filtered through celite and the filtrate is concentrated under reduced pressure. This crude product is used directly for the next step. See Example 11.

Workup

  1. filtrationThe mixture is filtered through celite
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c2ea4850f9c44aaa40dce7342ad9191
Source dataset
uspto-grants-1999_05
Patent number
US05902813

Reaction notes

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