N-methyl-2-pyrrolidone → Benzonitrile, o-(2-oxazolo(4,5-b)pyridinyl)-

HRID 259567Notes

Reaction equation

HRID 259567 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:11]([N:16]=1)=[N:12][CH:13]=[CH:14][CH:15]=2.[CH3:17][N:18]1CCCC1=O>>[C:17]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:11]([N:16]=1)=[N:12][CH:13]=[CH:14][CH:15]=2)#[N:18]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 49020322-(2-Bromophenyl)oxazolo[4,5-b]pyridine

Product 1

HCID 40322Benzonitrile, o-(2-oxazolo(4,5-b)pyridinyl)-

Conditions

Temperature
175 °C

Procedure

A mixture of 2.8 g. of 2-(2-bromophenyl)oxazolo[4,5-b]pyridine, 1.6 g. of cuprous cyanide and 15 ml. of N-methylpyrrolidinone was deairated by bubbling nitrogen through the mixture for 5 minutes. It was then heated to 175° C. in an oil-bath and held at that temperature for 5 hours under a nitrogen atmosphere and then allowed to cool to room temperature. The reaction mixture was treated with 75 ml. of 10% ammonium hydroxide and the resulting precipitate was collected. The precipitate was extracted with 100 ml. of boiling methylene chloride and the methylene chloride was evaporated. The residue was recrystallized from methylene chloride to give 2-(2-cyanophenyl)oxazolo[4,5-b]pyridine, m.p. 166°-167° C.

Workup

  1. additionA mixture of 2.8 g
  2. customby bubbling nitrogen through the mixture for 5 minutes
  3. temperatureto cool to room temperature
  4. additionThe reaction mixture was treated with 75 ml
  5. customof 10% ammonium hydroxide and the resulting precipitate was collected
  6. extractionThe precipitate was extracted with 100 ml
  7. customof boiling methylene chloride and the methylene chloride was evaporated
  8. customThe residue was recrystallized from methylene chloride

Sources & evidence

ORD record
ord-e854fc348b2c4effa8f9985412a1169e
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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