Nitric Acid → N-(2-ethyl-6-nitrophenyl)acetamide

HRID 2203212ノート

反応式

HRID 2203212 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:12])[CH3:11])[CH3:2].[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:13]([O-:15])=[O:14])[C:4]=1[NH:9][C:10](=[O:12])[CH3:11])[CH3:2]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 36332O-Ethylacetanilide

生成物 1

HCID 14147006N-(2-ethyl-6-nitrophenyl)acetamide収率 30.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a mixture of N-(2-ethylphenyl)acetamide (6.2 g, 38 mmol) in acetic acid (50 mL) was added dropwise fuming HNO3 (13 mL, 310 mmol) at a temperature of 50° C. to 55° C. The mixture was allowed to react at 55° C. for 2 hours and was subsequently cooled to RT, poured onto ice, and extracted with DCM. The organic layer was washed with water until the pH of the aqueous phase was >7. The organic layer was washed again with water, dried over Na2SO4, and the solvent evaporated. The residue was purified using flash chromatography eluting with MeOH/DCM (1:400) to give the title compound as a yellow solid (2.4 g, 30%; 48% purity). 1H NMR (400 MHz, CD3OD) δ 7.75 (1H, d, J=7.6 Hz), 7.62 (1H, d, J=7.6 Hz), 7.43 (1H, t, J=7.6 Hz), 2.71 (2H, q, J=7.6 Hz), 2.14 (3H, s), 1.21 (3H, t, J=7.6 Hz).

後処理

  1. customto react at 55° C. for 2 hours
  2. additionpoured onto ice
  3. extractionextracted with DCM
  4. washThe organic layer was washed with water until the pH of the aqueous phase
  5. washThe organic layer was washed again with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent evaporated
  8. customThe residue was purified
  9. washeluting with MeOH/DCM (1:400)

出典と根拠

ORDレコード
ord-01d251d5b06d44619d630daa386c2bf5
出典データセット
uspto-grants-2016_06
特許番号
US09365566B2

反応ノート

読み込み中…