3-Fluoro-4-(3-cyano-1-pyrrolyl)nitrobenzene → 5-Amino-2-(3-cyano-1-pyrrolyl)fluorobenzene

HRID 1167465Notes

Reaction equation

HRID 1167465 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:15]([O-])=O)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9]1>CO.[Pd]>[NH2:15][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9]2)=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 1

HCID 229960033-Fluoro-4-(3-cyano-1-pyrrolyl)nitrobenzene

Product 1

HCID 229961405-Amino-2-(3-cyano-1-pyrrolyl)fluorobenzene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Fluoro-4-(3-cyano-1-pyrrolyl)nitrobenzene (5.3 g, 22.9 mmnol) was dissolved in hot MeOH (250 ml) and palladium catalyst (10% on charcoal, 700 mg) added under a nitrogen atmosphere. The mixture was cooled and hydrogenated at atmospheric pressure for 3.5 hours. After filtration through celite, the solution was evaporated to dryness to give title product in sufficent purity for the next stage (4.6 g).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationAfter filtration through celite
  3. customthe solution was evaporated to dryness

Sources & evidence

ORD record
ord-312b9797beda4aba96ca2a5a0f066241
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

Loading…