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

HRID 1472973

반응식

HRID 1472973 반응식
[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]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 8359Isatoic Anhydride

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
41 °C

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-d55dd8fec5894921a6f37623787fd92b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012691B2

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