Nitric Acid → 6-Nitrofuro[3,2-c]pyridin-7-ol

HRID 911947Notes

Reaction equation

HRID 911947 reaction equation
[O:1]1[C:9]2[C:8]([OH:10])=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[N+:11]([O-])([OH:13])=[O:12]>>[N+:11]([C:7]1[N:6]=[CH:5][C:4]2[CH:3]=[CH:2][O:1][C:9]=2[C:8]=1[OH:10])([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 944Nitric Acid2×HCID 53486798Furo[3,2-c]pyridin-7-ol

Product 1

HCID 578124576-Nitrofuro[3,2-c]pyridin-7-olYield 26%

Conditions

Temperature
0 °C

Procedure

The reaction was conducted with 1 g starting material/10 mL 90% aq. nitric acid ratio. Reactions were run at 2×200 mg, 500 mg, 4×1.05 g scales. The nitric acid was cooled down to 0° C. and furo[3,2-c]pyridin-7-ol was added in portions slowly. The color of the reaction mixture turned to deep orange/red. The reaction mixture was stirred at 0° C. for 30 min. LC-MS showed complete consumption of the starting material. The mixture was poured into crashed ice to quench reaction, then extracted with DCM (3×10 mL for 200 mg scale). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, and concentrated under vacuum. The resulting yellow solid (1.83 g, 26% yield) was directly used in the next step. 1H NMR (CD3OD, 400 MHz): δ=7.16 (d, J=2.0 Hz, 1H), 8.18 (d, J=2.0 Hz, 1H), 8.39 (s, 1H). MS (ES+): 181.01 [MH+].

Workup

  1. customconsumption of the starting material
  2. additionThe mixture was poured
  3. customto quench
  4. customreaction
  5. extractionextracted with DCM (3×10 mL for 200 mg scale)
  6. washThe combined organic layers were washed with brine (10 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0d3d06a6af4c4a989dc48d9c81df7aab
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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