Nitric Acid → HCID 178526786, compound

HRID 2245614Notes

Reaction equation

HRID 2245614 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[N+:11]([O-])([OH:13])=[O:12].C(OCC)C>C(O)(=O)CC>[N+:11]([C:7]1[C:2]([OH:1])=[C:3]2[S:10][CH:9]=[CH:8][C:4]2=[N:5][CH:6]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 5074765Thieno[3,2-b]pyridin-7-ol

Product 1

HCID 178526786HCID 178526786, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
110 °C

Procedure

Commercially available 7-hydroxythieno[3,2-b]pyridine (9.9 g, 65.5 mmol) was dissolved in propionic acid (200 mL) and heated to 110° C., behind a bomb shield. 4.85 mL of fuming nitric acid (90%) was added over 2 minutes, during which time a copius precipitate formed. The thick suspension was brought to reflux (oil bath temperature ˜150° C.) for 1 h during which time an orange gas evolved (Caution: procedure should only be performed in a well ventilated hood). The reaction mixture was allowed to cool to room temperature and 200 mL of diethyl ether was added. The product was collected by filtration, washed with ˜400 mL of water, 300 mL of 1:1 diethyl ether/methanol, and dried to yield 9.5 g, (74%) of A2.1 as a tan powder. M.S. 197 (M+H)+ 100%.

Workup

  1. customformed
  2. temperatureto reflux (oil bath temperature ˜150° C.) for 1 h during which time an orange gas
  3. temperatureto cool to room temperature
  4. filtrationThe product was collected by filtration
  5. washwashed with ˜400 mL of water, 300 mL of 1:1 diethyl ether/methanol
  6. customdried
  7. customto yield 9.5 g, (74%) of A2.1 as a tan powder

Sources & evidence

ORD record
ord-b51ffba52f764745af15272e6c84818e
Source dataset
uspto-grants-2010_03
Patent number
US07683171B2

Reaction notes

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