Acetic Anhydride → 4-Nitrothiophene-2-carbonitrile

HRID 2196495

Reaction equation

HRID 2196495 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([C:11]1[CH:12]=[C:13]([CH:16]=O)[S:14][CH:15]=1)([O-:10])=[O:9].Cl.[NH2:19]O>N1C=CC=CC=1>[N+:8]([C:11]1[CH:12]=[C:13]([C:16]#[N:19])[S:14][CH:15]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 818857HCID 818857, compound

Product 1

HCID 8190444-Nitrothiophene-2-carbonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

Acetic anhydride (1.2 mL) was added to a mixture of aldehyde 1 (314.3 mg, 2.00 mmol) and hydroxylamine hydrochloride (277.6 mg, 4.00 mmol) in pyridine (1.5 mL) pre-heated at 95° C. according to the procedure of M. Bobosikova et al. (J. Chem. Soc., Perkin Trans. I, 2001, 680-689). After 2 h at 95° C. the mixture was cooled and poured over ice and the precipitate was filtered out and allowed to air dry. Nitrile 2 was obtained in 68% yield as beige solid 1H NMR (CDCl3) δ(ppm): 8.51 (s, 1H), 8.14 (s, 1H).

Workup

  1. temperatureAfter 2 h at 95° C. the mixture was cooled
  2. additionpoured over ice
  3. filtrationthe precipitate was filtered out
  4. customto air dry

Sources & evidence

ORD record
ord-e5a193ca93074e70b905fe9ec4a66206
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Linked notes

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