Water → HCID 23326336, compound

HRID 1904044Notes

Reaction equation

HRID 1904044 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[CH3:14])[C:2]#[CH:3].[OH2:15].[K+].[Br-]>N1C=CC=CC=1CO.CC([O-])=O.CC([O-])=O.[Cu+2].O>[CH3:14][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:15])=[CH:7][C:6]=1[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 253877Potassium BromideHCID 23326340HCID 23326340, compound

Product 1

HCID 23326336HCID 23326336, 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, 15 ml) was added N-(2-propynyl)-2-methyl-4-nitroaniline (1.00 g, 5.26×10-3 mole). The reaction mixture was stirred at 50° C. for two hours. The mixture was poured into excess water and filtered. The crude solid was recrystallized from nitromethane to afford yellow crystals. Yield: 0.70 g (71%). The material did not melt below 200° C. but turned red at 150° C. I.R. (KBr): 3390 (NH), 1585 and 1280 cm-1 (Ar-NO2).

Workup

  1. filtrationfiltered
  2. customThe crude solid was recrystallized from nitromethane
  3. customto afford yellow crystals
  4. customdid not melt below 200° C.
  5. customturned red at 150° C

Sources & evidence

ORD record
ord-fb9c7c88787f4bd7b08ef984339e0243
Source dataset
uspto-grants-1984_03
Patent number
US04439514

Reaction notes

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