Nitric Acid → 5-Methyl-6-nitro-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 1603008

反応式

HRID 1603008 の反応式
[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[O:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15]>OS(O)(=O)=O>[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[O:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

生成物 1

HCID 219011545-Methyl-6-nitro-1H-benzo[d][1,3]oxazine-2,4-dione

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-methyl-4H-3,1-benzoxazin-2,4-dione (20 g, 113 mmol) in 150 mL of concentrated H2SO4, cooled to -15° C., was added 7.83 g of 90% w/w HNO3 (in 30 mL of conc. H2SO4) dropwise at such a rate to keep the internal temperature below 5° C. After the addition was complete, the reaction was stirred at 0° C. for an additional 20 minutes then quenched by pouring the reaction mixture over crushed ice. Following further dilution with water, the resulting precipitate was filtered, washed with water, resuspended in water then filtered and washed again with water affording 15.1 g (60%) of 5-methyl-6-nitro-4H-3,1-benzoxazin-2,4-dione, after drying: Anal. Calc'd. for C9H6N2O5 : C, 48.66; H, 2.72; N, 12.61. Found: C, 48.19; H, 2.54; N, 12.51.

後処理

  1. customthe internal temperature below 5° C
  2. additionAfter the addition
  3. customthen quenched
  4. additionby pouring the reaction mixture
  5. customover crushed ice
  6. filtrationthe resulting precipitate was filtered
  7. washwashed with water
  8. filtrationthen filtered
  9. washwashed again with water affording 15.1 g (60%) of 5-methyl-6-nitro-4H-3,1-benzoxazin-2,4-dione
  10. customafter drying

出典と根拠

ORDレコード
ord-21765759bac741c69e4bc6a176b34946
出典データセット
uspto-grants-1999_11
特許番号
US05985872

関連ノート

読み込み中…