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

HRID 2203207

反応式

HRID 2203207 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2698caa59a6e4839b7403b82b48cf81c
出典データセット
uspto-grants-2016_06
特許番号
US09365566B2

関連ノート

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