Nitric Acid → N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide

HRID 2203207

반응식

HRID 2203207 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>O(C(C)=O)C(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N+:13]([O-:15])=[O:14])[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 2737623N-(4-Fluoro-2-methylphenyl)acetamide

생성물 1

HCID 54330341N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

To a mixture of N-(4-fluoro-2-methylphenyl)acetamide (19 g, 113.1 mmol, 1 eq) and (CH3CO)2O (190 mL) was added HNO3 (11.4 mL, 1.0 eq) dropwise at 0° C. The reaction mixture was allowed to warm to RT overnight and was subsequently poured onto ice and extracted with DCM. The organic phase was washed with aqueous NaHCO3 until the pH of the aqueous layer was >7. The organic phase was washed with water and then dried over Na2SO4. The solvent was evaporated to give the title compound as a crude solid (20 g, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.82 (1H, s), 7.71 (1H, dd, J1=2.8 Hz, J2=8.0 Hz), 7.56 (1H, dd, J1=2.8 Hz, J2=9.2 Hz), 2.32 (3H, s), 2.02 (3H, s).

후처리

  1. additionwas subsequently poured onto ice
  2. extractionextracted with DCM
  3. washThe organic phase was washed with aqueous NaHCO3 until the pH of the aqueous layer
  4. washThe organic phase was washed with water
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-2698caa59a6e4839b7403b82b48cf81c
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365566B2

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