Nitric Acid → 2H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro-

HRID 1472973

Reaction equation

HRID 1472973 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C>[N+:13]([C:10]1[CH:11]=[C:1]2[C:2]([O:4][C:5](=[O:12])[NH:6][C:7]2=[CH:8][CH:9]=1)=[O:3])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 8359Isatoic Anhydride

Product 1

HCID 208212H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro-Yield 87.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
41 °C

Procedure

Isatoic Anhydride (25.0 g, 153.25 mmol) is suspended in acetic acid (50 mL) with efficient stirring. The reaction vessel is placed in a pre-heated oil bath at 40° C. and red fuming nitric acid (99.5%, 75 mL, 1.67 mol) is added over 35 minutes (Caution: Exothermic). The reaction mixture is stirred for an additional 4 hours at 38-44° C., then cooled to 20° C. using an ice bath. The reaction mixture is poured on ice (400 mL). After the ice melts, the yellow solid is isolated by vacuum filtration and washed with cold water (5×100 mL). The yellow solid is dried under high vacuum to constant weight at 60-70° C. affording 27.92 g (87%) of product; 1H-NMR (300 MHz, DMSO-d6); δ12.33 (s, 1H), 8.58 (d, J=2.5 Hz, 1H), 8.53 (dd, J=2.6 Hz, 9.0 Hz, 1H), 7.31 (d, J=8.9 Hz, 1H).

Workup

  1. customThe reaction vessel is placed in a pre-heated oil bath at 40° C.
  2. temperaturecooled to 20° C.
  3. additionThe reaction mixture is poured on ice (400 mL)
  4. customthe yellow solid is isolated by vacuum filtration
  5. washwashed with cold water (5×100 mL)
  6. customThe yellow solid is dried under high vacuum to constant weight at 60-70° C.

Sources & evidence

ORD record
ord-d55dd8fec5894921a6f37623787fd92b
Source dataset
uspto-grants-2015_04
Patent number
US09012691B2

Linked notes

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