Nitric Acid → HCID 86669351, compound

HRID 924981Notes

Reaction equation

HRID 924981 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:11])=[C:7]([CH:10]=1)[C:8]#[N:9])=[O:2].[N+:12]([O-])([OH:14])=[O:13].C(OCC)(=O)C>C(O)(=O)C>[CH:1]([C:3]1[CH:4]=[C:5]([N+:12]([O-:14])=[O:13])[C:6]([OH:11])=[C:7]([CH:10]=1)[C:8]#[N:9])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 221125485-Formyl-2-hydroxybenzonitrile

Product 1

HCID 86669351HCID 86669351, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-formyl-2-hydroxybenzonitrile (200 mg, 1.36 mmol) in acetic acid (4 mL) was added slowly concentrated nitric acid (0.8 mL) at 0° C. The resulting mixture was stirred for 5 hours. Then the mixture was poured into ice-water (40 mL) and ethyl acetate (100 mL). Organic was washed with brine (80 mL), dried over sodium sulfate and evaporated in vacuo, followed by column chromatography (petroleum ether/ethyl acetate=3:1) to give Intermediate 61 (250 mg, yield 96%).

Workup

  1. washOrganic was washed with brine (80 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-c52dacacf6314942868c0be681e0f6f0
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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