Pentanoic Acid → HCID 178441530, compound

HRID 344072Notes

Reaction equation

HRID 344072 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].[C:12](O)(=O)[CH2:13][CH2:14][CH2:15][CH3:16]>P(Cl)(Cl)(Cl)=O>[CH2:13]([C:12]1[NH:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[N:11]=1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 7991Pentanoic AcidHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 178441530HCID 178441530, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

11.5 g (0.075 mol) of 4-nitro-o-phenylenediamine are introduced in portions at ambient temperature into a mixture of 8.66 g (0.085 mol) of valeric acid and 120 ml of phosphorus oxychloride. The mixture is then heated for 3 hours under reflux. The reaction mixture is separated in 1.5 kg of iced water, rendered alkaline using concentrated ammonia and extracted three times using 500 ml of ethyl acetate. The organic phase is separated off, dried using magnesium sulphate and rotary evaporated. The oily residue is purified over a silica gel column (grain size: 0.063-0.2 mm, eluting agent: methylene chloride/0-2% ethanol). The homogeneous fractions are evaporated to dryness.

Workup

  1. temperatureThe mixture is then heated for 3 hours
  2. temperatureunder reflux
  3. customThe reaction mixture is separated in 1.5 kg of iced water
  4. extractionextracted three times
  5. customThe organic phase is separated off
  6. customdried
  7. customThe oily residue is purified over a silica gel column (grain size: 0.063-0.2 mm, eluting agent: methylene chloride/0-2% ethanol)
  8. customThe homogeneous fractions are evaporated to dryness

Sources & evidence

ORD record
ord-6388d30c93ff4985a1896dd4f8019515
Source dataset
uspto-grants-1999_01
Patent number
US05864043

Reaction notes

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