Nitric Acid → 7-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 518972ノート

反応式

HRID 518972 の反応式
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[F:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 944Nitric AcidHCID 137312957-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one

生成物 1

HCID 137312977-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one収率 92%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒2 回

反応条件

温度
-10 °C

実験手順

To a solution of 7-fluoro-4H-benzo[1,4]oxazin-3-one (3.00 g, 17.95 mmol) in concentrated H2SO4 (12 mL) at −10° C. was added a mixture of fuming nitric acid (1.131 g, 17.95 mmol, 0.75 mL) and concentrated H2SO4 (0.75 mL) dropwise, keeping the internal temperature below 0° C. After addition, the reaction mixture was stirred at −10° C. for 10 min. The reaction mixture was poured onto crushed ice (200 g) with care. The precipitate was collected by filtration, washed with water (50 mL) and dried in vacuo to give 7-fluoro-6-nitro-4H-benzo[1,4]oxazin-3-one as a light yellow solid (3.5 g, 92%). 1H NMR (DMSO-d6, 400 MHz): δ 11.02 (s, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.23 (d, J=12.0 Hz, 1H), 4.77 (s, 2H).

後処理

  1. customthe internal temperature below 0° C
  2. additionAfter addition
  3. additionThe reaction mixture was poured
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (50 mL)
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-3997ac9bef4f43229d070b32b70ed8aa
出典データセット
uspto-grants-2015_08
特許番号
US09115151B2

反応ノート

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