Malonic Acid → 3-(5-Cyano-2-thiophenyl)-propenoic acid

HRID 477171

Reaction equation

HRID 477171 reaction equation
[C:1]([C:3]1[S:7][C:6]([CH:8]=O)=[CH:5][CH:4]=1)#[N:2].C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13]>N1C=CC=CC=1.N1CCCCC1>[C:1]([C:3]1[S:7][C:6]([CH:8]=[CH:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 867Malonic Acid2×HCID 122800045-Formylthiophene-2-Carbonitrile

Product 1

HCID 679354333-(5-Cyano-2-thiophenyl)-propenoic acid

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8082PiperidineSolvent

Procedure

A stirred solution of 5-cyano-2-thiophene carboxaldehyde (3.3 g) and malonic acid (2.5 g) in pyridine (35 ml) and piperidine (0.7 ml) was heated under reflux for 2 hours adding further malonic acid (1.3 g) after 1 hour. The solution was evaporated and the residue was stirred with M hydrochloric acid solution (100 ml) to give a pale solid which was washed with water and dried, m.p. ca 260° C. (subliming).

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solution was evaporated
  3. customto give a pale solid which
  4. washwas washed with water
  5. customdried

Sources & evidence

ORD record
ord-5974a54b8de34cc1931a9ce2ebd93e8e
Source dataset
uspto-grants-1989_12
Patent number
US04886885

Linked notes

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