Water → HCID 23326341, compound

HRID 1904048Notes

Reaction equation

HRID 1904048 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])[C:2]#[CH:3].[OH2:18]>N1C=CC=CC=1CO.CC([O-])=O.CC([O-])=O.[Cu+2].O>[N+:15]([C:6]1[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]([F:11])=[CH:10][C:5]=1[NH:4][CH2:1][C:2]#[C:3][C:3]#[C:2][CH2:1][NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:13])=[O:18])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])([O-:17])=[O:16]

Participants

5

Reactant 2

HCID 962WaterHCID 23326339HCID 23326339, compound

Product 1

HCID 23326341HCID 23326341, compound

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 11474PiconolSolvent

Procedure

To a suspension of Cu(OAc)2.H2O (1.5 g) in pyridinemethanol (1:1, 10 ml) was added N-(2-propynyl)-2,4-dinitro-5-fluoroaniline (1.00 g, 4.18×10-3 mole). The reaction mixture was stirred at room temperature for 17 hours. The mixture was poured into excess water and filtered. The crude solid was chromatographed on a silica column, eluting with chloroform ethyl acetate. Soxhlet recrystallization of the resulting solid from ethyl acetate afforded yellow crystals, m.p. 225° C. dec. Yield: 0.21 g (12%). I.R. (KBr): 3360 (NH), 1680 and 1315 cm-1 (Ar-NO2).

Workup

  1. filtrationfiltered
  2. customThe crude solid was chromatographed on a silica column
  3. washeluting with chloroform ethyl acetate
  4. customSoxhlet recrystallization of the resulting solid from ethyl acetate afforded yellow crystals, m.p. 225° C. dec

Sources & evidence

ORD record
ord-3aabac2bc5f04445b62ecffc04eee553
Source dataset
uspto-grants-1984_03
Patent number
US04439514

Reaction notes

Loading…