Aniline → HCID 302917, compound

HRID 2227188Notes

Reaction equation

HRID 2227188 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[F:13][B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](O)(CC1)CC2.C(#N)C.NC1C=CC=CC=1>C(OCC)(=O)C>[Cl:9][C:8]1[C:7]([F:13])=[C:5]([C:4]([N+:10]([O-:12])=[O:11])=[CH:3][C:2]=1[Cl:1])[NH2:6]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6342AcetonitrileHCID 811494,5-Dichloro-2-nitroanilineHCID 27373291-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

Product 1

HCID 302917HCID 302917, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4,5-Dichloro-2-nitroaniline (9.8 g, 47.4 mmol), 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (18.5 g, 57.4 mmol, Allied Signal, Buffalo), and acetonitrile (300 mL) were combined and the mixture was heated to reflux for several hours. After thin-layer chromatography showed that no starting aniline remained, the mixture was allowed to cool to rt and was poured into ethyl acetate, causing a precipitate to form. The mixture was filtered through a pad of Celite, purified by silica gel and the solvents were removed in vacuo to provide a brown solid (3.9 g, 37%); 1H NMR (DMSO-d6) δ: 8.11 (d, J=2.2 Hz, 1H, Ar—H), 7.67 (br s, 2H, NH2).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for several hours
  3. customto form
  4. filtrationThe mixture was filtered through a pad of Celite
  5. custompurified by silica gel
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-5062431c594f452da2c29722f5bb47c4
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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