Nitric Acid → HCID 67406031, compound

HRID 467999Notes

Reaction equation

HRID 467999 reaction equation
[N+:1]([O-:4])(O)=[O:2].[B:5]1([OH:15])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][O:6]1>>[N+:1]([C:12]1[CH:13]=[CH:14][C:9]2[CH2:8][CH2:7][O:6][B:5]([OH:15])[C:10]=2[CH:11]=1)([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 441193503,4-Dihydro-1H-2,1-benzoxaborinin-1-ol

Product 1

HCID 67406031HCID 67406031, compoundYield 44%

Conditions

Temperature
-42.5 °C

Procedure

To 4.0 mL fuming HNO3 at −45° C. was added 3,4-dihydro-benzo[c][1,2]oxaborinin-1-ol (497 mg, 3.4 mmol) in small portions while maintaining the reaction temperature between −40 to −45° C. Once the addition was complete the resulting solution was allowed to stir at −45° C. for an additional 10 min before poured into crushed ice (20 g). The ice mixture was allowed to warm up to room temperature gradually and the precipitate was collected by filtration and washed with H2O to give 7-nitro-3,4-dihydro-benzo[c][1,2]oxaborinin-1-ol as a white powder. 1H NMR (acetone) δ: 8.51 (d, J=2.5 Hz, 1H), 8.24 (dd, J=8.3, 2.6 Hz, 1H), 7.75 (s, 1H), 7.50 (d, J=8.4 Hz, 1H), 4.19 (t, J=6.0 Hz, 2H), 3.07 (t, J=6.0 Hz, 2H). Amount obtained: 286 mg, 44% yield.

Workup

  1. additionOnce the addition
  2. additionbefore poured
  3. temperatureto warm up to room temperature gradually
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with H2O

Sources & evidence

ORD record
ord-614cb08ce7404e21ad9410a8a7c4e1c4
Source dataset
uspto-grants-2014_01
Patent number
US08623911B2

Reaction notes

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