Nitric Acid → 6-Nitrothieno[3,2-b]pyridin-7-ol

HRID 580536Notes

Reaction equation

HRID 580536 reaction equation
[S:1]1[C:9]2[C:8](=[O:10])[CH:7]=[CH:6][NH:5][C:4]=2[CH:3]=[CH:2]1.[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)CC.CCOCC>[N+:11]([C:7]1[C:8](=[O:10])[C:9]2[S:1][CH:2]=[CH:3][C:4]=2[NH:5][CH:6]=1)([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 5074765Thieno[3,2-b]pyridin-7-ol

Product 1

HCID 136010926-Nitrothieno[3,2-b]pyridin-7-olYield 78%

Reagents, catalysts & solvents 2

HCID 1032Propionic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3.1 g of thieno[3,2-b]pyridin-7(4H)-one 13 in 90 ml of propionic acid is added 1.5 ml of fuming nitric acid at 110° C. with stirring and the mixture is refluxed for 1 hour. The cooled mixture is diluted with 50 ml of ether and the resulting crystals are collected by filtration, washed with water and ether-methanol, and dried to give 3.13 g (78%) of Compound 14. Recrystallization from dimethyl sulfoxide-methanol affords colorless crystals melting at 328°-331° C. (dec.).

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. filtrationthe resulting crystals are collected by filtration
  3. washwashed with water and ether-methanol
  4. customdried

Sources & evidence

ORD record
ord-ac7dda8f1ff04c569e7abcef6f2f493a
Source dataset
uspto-grants-1988_06
Patent number
US04753951

Reaction notes

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