N-methyl-2-pyrrolidone → 5-Cyano-2-phenyloxazolo[5,4-b]pyridine

HRID 259568Notes

Reaction equation

HRID 259568 reaction equation
Cl[C:2]1[N:7]=[C:6]2[O:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:17][N:18]1C(=O)CCC1>>[C:17]([C:2]1[N:7]=[C:6]2[O:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1)#[N:18]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 22754788HCID 22754788, compound

Product 1

HCID 227548215-Cyano-2-phenyloxazolo[5,4-b]pyridine

Conditions

Temperature
175 °C

Procedure

A mixture of 2.3 g. of 5-chloro-2-phenyloxazolo[5,4-b]pyridine, 1.6 g. of cuprous cyanide and 15 ml. of N-methyl pyrrolidinone is stirred under nitrogen and then heated in an oil bath of 175° C. (bath temperature). It is maintained at that temperature for 5 hours. The cooled, dark mixture is diluted with 75 ml. of 10% ammonium hydroxide and a dark precipitate removed by filtration. The solid is extracted with methylene dichloride. The methylene dichloride is evaporated and the residue crystallized from ethyl acetate.

Workup

  1. additionA mixture of 2.3 g
  2. temperatureIt is maintained at that temperature for 5 hours
  3. additionThe cooled, dark mixture is diluted with 75 ml
  4. customof 10% ammonium hydroxide and a dark precipitate removed by filtration
  5. extractionThe solid is extracted with methylene dichloride
  6. customThe methylene dichloride is evaporated
  7. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-068dec5f5a8047449381028e79f4cdde
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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