2-(3-Nitrophenyl)pyrazine → 3-(Pyrazin-2-yl)aniline

HRID 1835442Notes

Reaction equation

HRID 1835442 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>O1CCCC1.C(O)C.[Pd]>[N:11]1[CH:12]=[CH:13][N:14]=[CH:15][C:10]=1[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1]

Participants

5

Reactant 1

HCID 235036832-(3-Nitrophenyl)pyrazine

Product 1

HCID 235036723-(Pyrazin-2-yl)anilineYield 96.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-(3-nitrophenyl)pyrazine (500 mg) in tetrahydrofuran (5 ml) and ethanol (5 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 200 mg) under hydrogen atmosphere for 6 hours. The catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from dichloromethanediisopropyl ether to give 3-(pyrazin-2-yl)aniline (410 mg, 96.5%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from dichloromethanediisopropyl ether

Sources & evidence

ORD record
ord-205127d164f34fa3a0250f281e9474e5
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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