Nitric Acid → N-(4-ethyl-2-nitrophenyl)acetamide

HRID 2064654노트

반응식

HRID 2064654 반응식
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([NH:7][C:8](=[O:10])[CH3:9])=[CH:5][CH:4]=1)[CH3:2].[N+:13]([O-])([OH:15])=[O:14]>C(OC(=O)C)(=O)C.C(O)(=O)C>[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([NH:7][C:8](=[O:10])[CH3:9])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1)[CH3:2]

참가 물질

5

반응물 2

HCID 944Nitric AcidHCID 72893N-(4-Ethylphenyl)acetamide

생성물 1

HCID 15919553N-(4-ethyl-2-nitrophenyl)acetamide

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 7918Acetic Anhydride용매

반응 조건

온도
0 °C

실험 절차

A stirred solution of 4-ethyl-N-acetyl-aniline [3 g, Reference Example 33(a)] in acetic anhydride (8 mL) and acetic acid (4 mL), at −5° C., was treated dropwise with a mixture of acetic acid (1.75 mL) and concentrated nitric acid (1.22 mL). The mixture was warmed to 0° C., then stirred at 0° C. for 2 hours and then poured onto water. This mixture was evaporated and the resulting oil was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate and then evaporated. The residual oil was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (2:5) to give 4-ethyl-2-nitro-N-acetyl-aniline (1.4 g) as an orange solid.

후처리

  1. additionpoured onto water
  2. customThis mixture was evaporated
  3. customthe resulting oil was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. additionThe residual oil was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (2:5)

출처 및 근거

ORD 기록
ord-ec9f763cebda464c9b3df8bce9755abc
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288425B2

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