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

HRID 1472973

反応式

HRID 1472973 の反応式
[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]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 8359Isatoic Anhydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
41 °C

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-d55dd8fec5894921a6f37623787fd92b
出典データセット
uspto-grants-2015_04
特許番号
US09012691B2

関連ノート

読み込み中…