Nitric Acid → HCID 14207939, compound

HRID 580530Notes

Reaction equation

HRID 580530 reaction equation
[S:1]1[C:5]2[NH:6][CH:7]=[CH:8][C:9](=[O:10])[C:4]=2[CH:3]=[CH:2]1.[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)CC>[N+:11]([C:8]1[C:9](=[O:10])[C:4]2[CH:3]=[CH:2][S:1][C:5]=2[NH:6][CH:7]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 12395107HCID 12395107, compound

Product 1

HCID 14207939HCID 14207939, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3.4 g of thieno[2,3-b]pyridin-4(7H)-one 5 in 105 ml of propionic acid is added 2.79 g of concentrated nitric acid (d=1.38) at 100° C., and then the mixture is stirred at 130° C. (bath temperature) for 1 hour. After cooling the reaction mixture, the resulting precipitate is collected by filtration and washed successively with water, methanol and acetone to afford 3.4 g (77%) of Compound 6 as pale yellow crytals melting at 288°-291° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe resulting precipitate is collected by filtration
  3. washwashed successively with water, methanol and acetone

Sources & evidence

ORD record
ord-f73d96ec921541e5a5efc4ebed2293c1
Source dataset
uspto-grants-1988_06
Patent number
US04753951

Reaction notes

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