HCID 28826183, compound → HCID 28994099, compound

HRID 537845Notes

Reaction equation

HRID 537845 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([NH:6][CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[C:4]([N+:17]([O-])=O)[CH:3]=1>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]([NH:6][CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 28826183HCID 28826183, compound

Product 1

HCID 28994099HCID 28994099, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-chloro-N-[3-(1H-imidazol-1-yl)propyl]-2-nitroaniline (11, 5 g, 17.8 mmol) was dissolved in 100 mL methanol (MeOH) and Palladium on activated carbon (10%, 120 mg, 0.1 eq.) was added under nitrogen atmosphere. The solution was hydrogenated at 1 bar for 16 hours. The reaction was filtered over celite and the filtrate concentrated in vacuo and purified by flash chromatography (gradient 0 to 10% methanol in CH2Cl2) to give 4-chloro-N1-[3-(1H-imidazol-1-yl)propyl]benzene-1,2-diamine (12, 2.18 g, 49%) as a solid; LCMS m/z=251 (M+H)+

Workup

  1. filtrationThe reaction was filtered over celite
  2. concentrationthe filtrate concentrated in vacuo
  3. custompurified by flash chromatography (gradient 0 to 10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-7d405b59a17b4c2ea68e40470e387606
Source dataset
uspto-grants-2014_10
Patent number
US08865705B2

Reaction notes

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