Water → HCID 23326343, compound

HRID 1904052Notes

Reaction equation

HRID 1904052 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])[C:2]#[CH:3].[OH2:17].[K+].[Br-]>N1C=CC=CC=1CO.CC([O-])=O.CC([O-])=O.[Cu+2].O>[N+:14]([C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[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]=[CH:9][C:8]([N+:11]([O-:12])=[O:17])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 962WaterHCID 253877Potassium BromideHCID 7514113HCID 7514113, compound

Product 1

HCID 23326343HCID 23326343, compound

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 11474PiconolSolvent

Conditions

Temperature
50 °C

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-dinitroaniline (1.00 g, 4.52×10-3 mole). The reaction mixture was stirred at 50° C. for 30 minutes. The mixture was poured into excess water, and filtered. The crude solid was recrystallized from nitromethane to afford pale green crystals. Yield: 0.86 g (86%). The compound failed to melt below 200° C. but changed from green to bronze color at 120° C. It could be recrystallized from dioxane to give a different crystal form, appearing as orange crystals which turn deep orange at 140° C. I.R. (KBr): 3380 (NH), 1617, 1592, 1333 and 1312 cm-1 (Ar-NO2).

Workup

  1. filtrationfiltered
  2. customThe crude solid was recrystallized from nitromethane
  3. customto afford pale green crystals
  4. customto melt below 200° C.
  5. customat 120° C
  6. customIt could be recrystallized from dioxane
  7. customto give a different crystal form
  8. customturn deep orange at 140° C

Sources & evidence

ORD record
ord-d76aed5a894241d382a9037a58bb6df3
Source dataset
uspto-grants-1984_03
Patent number
US04439514

Reaction notes

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