Nitric Acid → HCID 178524776, compound

HRID 2117361Notes

Reaction equation

HRID 2117361 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[N+:11]([O-])([OH:13])=[O:12]>>[OH:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178418479HCID 178418479, compound

Product 1

HCID 178524776HCID 178524776, compound

Conditions

Temperature
50 °C

Procedure

To a 250 mL flask were added 6-hydroxynicotinic acid (20 g, Aldrich) and 100 mL of red fuming nitric acid. The mixture was slowly heated to 50° C. (bath temperature) and stirred at this temperature for 8 h. Then the temperature was slowly raised to 80° C. and the mixture was stirred for another 7 h. The mixture was cooled to rt overnight and the yellow precipitate was collected by filtration, washed with water (10 mL) and dried. LC-MS: >95% pure. 1H NMR (CD3OD, 400 MHz): δ=8.45 (d, J=2.5 Hz, 1H), 8.85 (d, J=2.5 Hz, 1H).

Workup

  1. temperatureThen the temperature was slowly raised to 80° C.
  2. stirringthe mixture was stirred for another 7 h
  3. temperatureThe mixture was cooled to rt overnight
  4. filtrationthe yellow precipitate was collected by filtration
  5. washwashed with water (10 mL)
  6. customdried

Sources & evidence

ORD record
ord-8e726380570b4c07b85c0076aa9eb2cf
Source dataset
uspto-grants-2008_10
Patent number
US07442709B2

Reaction notes

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