Cyclopropanecarboxylic acid → HCID 178526476, compound

HRID 1880660Notes

Reaction equation

HRID 1880660 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[CH:12]1([C:15](O)=O)[CH2:14][CH2:13]1>>[CH:12]1([C:15]2[NH:10][C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=3[N:11]=2)[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 15655Cyclopropanecarboxylic acidHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 178526476HCID 178526476, compoundYield 98%

Procedure

By analogy with a described method (WO 96/04270), a solution of 5 g (32.65 mmol) of 4-nitro-1,2-phenylenediamine in 77 ml (0.979 mol) of cyclopropanecarboxylic acid is stirred at reflux for 14 hours. The reaction mixture is then concentrated under reduced pressure and taken up in 150 ml of ethyl acetate and 100 ml of sodium hydrogen carbonate. The organic phase is washed with 100 ml of water and then with 50 ml of saturated sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. 6.5 g of a brown oil are obtained, and are used without further purification in the following step.

Workup

  1. temperatureat reflux for 14 hours
  2. concentrationThe reaction mixture is then concentrated under reduced pressure
  3. washThe organic phase is washed with 100 ml of water
  4. dry with materialwith 50 ml of saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa0076985cbc40d9bb882fab39060329
Source dataset
uspto-grants-2012_11
Patent number
US08318775B2

Reaction notes

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