HCID 18985086, compound → HCID 18985102, compound

HRID 1439926Notes

Reaction equation

HRID 1439926 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>[Fe].C(O)(=O)C>[NH2:1][C:4]1[C:12]2[O:11][C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 18985086HCID 18985086, compound

Product 1

HCID 18985102HCID 18985102, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

4 ml of 10% acetic acid was added to 7-nitro-2-(3-pyridyl)benzoxazole prepared in Reference Example 3, and 200 mg of powdered iron was added by portions with stirring at room temperature. The mixture was heated to 100° C. in an oil bath and stirred for 2 hr. The reaction mixture was filtered through Celite and washed with a small amount of dilute hydrochloric acid. The filtrate was neutralized with an aqueous sodium hydroxide solution, the product was extracted with ethyl acetate, and the organic layer was dried. The organic solvent was removed by evaporation to provide 153 mg of the intended title compound.

Workup

  1. additionwas added by portions
  2. temperatureThe mixture was heated to 100° C. in an oil bath
  3. stirringstirred for 2 hr
  4. filtrationThe reaction mixture was filtered through Celite
  5. washwashed with a small amount of dilute hydrochloric acid
  6. extractionthe product was extracted with ethyl acetate
  7. customthe organic layer was dried
  8. customThe organic solvent was removed by evaporation

Sources & evidence

ORD record
ord-9fc1c10b99cc4c44a9118a93e4e633a9
Source dataset
uspto-grants-1996_03
Patent number
US05496853

Reaction notes

Loading…