Hydrochloric Acid → 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile

HRID 236346Notes

Reaction equation

HRID 236346 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6](#N)[CH2:7][C:8]#[N:9].Cl.C(OCC)(=[O:14])C>CCOCC.O>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:7][C:8]#[N:9])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 8027PyrroleHCID 8857Ethyl Acetate

Product 1

HCID 111943553-oxo-3-(1H-pyrrol-2-yl)propanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Into an ice-chilled solution of 30 g of pyrrole and 30 g of malononitrile in 800 ml of dry ether is passed by HCl for 20 minutes. After standing several hours the suspension is filtered to give 65 g of orange-brown, water-soluble solid. The solution of 50 g of this intermediate (the enamine nitrile hydrochloride) in 600 ml of water is covered with 400 ml of ethyl acetate and stirred for 21/2 hours at room temperature. The organic layer is separated, dried (MgSO4) and evaporated to give crystals, m.p. 77°-9°; additional product is obtained by warming the aqueous layer on steam cone for 1/2 hour and extracting with ethyl acetate. Recrystallization from water gives 2-pyrroloylacetonitrile, m.p. 79°-81°.

Workup

  1. waitAfter standing several hours
  2. filtrationthe suspension is filtered
  3. customto give 65 g of orange-brown, water-soluble solid
  4. customThe organic layer is separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give crystals, m.p. 77°-9°
  8. customadditional product is obtained
  9. temperatureby warming the aqueous layer on steam cone for 1/2 hour
  10. extractionextracting with ethyl acetate
  11. customRecrystallization from water

Sources & evidence

ORD record
ord-c02a5b1f77444550b02b55b84b8163a7
Source dataset
uspto-grants-1987_02
Patent number
US04644010

Reaction notes

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