Isoamylamine → HCID 21476259, compound

HRID 2293112Notes

Reaction equation

HRID 2293112 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].F[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]>C1COCC1>[CH3:5][CH:4]([CH3:6])[CH2:3][CH2:2][NH:1][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 21476259HCID 21476259, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-amino-3-methylbutane (1.5 g) in THF (20 ml) was dropped into a solution of 2-fluoronitrobenzene (2.4 g) in THF (20 ml), at 23° under a nitrogen atmosphere. The mixture was stirred at 23° for 3 h, then heated at reflux for 1.5 h. The mixture was allowed to cool to 23°, then concentrated under vacuum to give a crude compound which was purified by flash chromatography (eluting with CH-EA 9:1) to give the title compound as a yellow oil (2.12 g). T.l.c. CH-EA (4:1) Rf=0.79.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 h
  3. temperatureto cool to 23°
  4. concentrationconcentrated under vacuum
  5. customto give a crude compound which
  6. customwas purified by flash chromatography (eluting with CH-EA 9:1)

Sources & evidence

ORD record
ord-56e48e9f73814aa58ee3c9275f50364d
Source dataset
uspto-grants-1997_11
Patent number
US05686449

Reaction notes

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