Nitric Acid → HCID 22602613, compound

HRID 2307839Notes

Reaction equation

HRID 2307839 reaction equation
[B:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[O:5]1)([OH:3])[OH:2].[N+:14]([O-])([OH:16])=[O:15]>>[N+:14]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:6](=[O:7])[O:5][CH:4]2[B:1]([OH:2])[OH:3])([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 54299518HCID 54299518, compound

Product 1

HCID 22602613HCID 22602613, compoundYield 71%

Procedure

Boronophthalide (2.86 g, 21.4 mmol) is added to 18.6 mL of chilled, fuming nitric acid (at 45° C.) in portions over 4 minutes with stirring. The reaction is quenched with ice and water (40 g and 60 mL), then the resulting pale yellow solid is collected on a Büchner filter and washed with 75 mL of water. Drying the solid in vacuo over P2O5 gives 2.72 g (15.2 mmol, 71.0%) 5-Nitroboronophthalide as a pale yellow solid (m.p. 178-179° C.).

Workup

  1. temperatureof chilled
  2. customThe reaction is quenched with ice and water (40 g and 60 mL)
  3. customthe resulting pale yellow solid is collected on a Büchner
  4. filtrationfilter
  5. washwashed with 75 mL of water
  6. dry with materialDrying the solid in vacuo over P2O5

Sources & evidence

ORD record
ord-3388302191bc49959d24682314044642
Source dataset
uspto-grants-2004_12
Patent number
US06833274B2

Reaction notes

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