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

HRID 518972노트

반응식

HRID 518972 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매2회

반응 조건

온도
-10 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3997ac9bef4f43229d070b32b70ed8aa
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115151B2

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