Nitric Acid → HCID 86721358, 화합물

HRID 869528

반응식

HRID 869528 반응식
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:5].C(OC(=O)CCC)(=O)CCC.[N+:28]([O-])([OH:30])=[O:29].[OH-].[Na+]>O>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:16]([N+:28]([O-:30])=[O:29])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:5]

참가 물질

6

반응물 4

HCID 944Nitric AcidHCID 7798Butyric anhydrideHCID 14798Sodium HydroxideHCID 836497Methyl 2-(2-methoxyacetamido)benzoate

생성물 1

HCID 86721358HCID 86721358, 화합물수율 51%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

[step 1] Methyl 2-(2-methoxyacetamido)benzoate (U.S. Pat. No. 5,091,403; 3.0 g, 13.4 mmol) was suspended in butyric anhydride (12.7 mL, 134.0 mmol), fuming nitric acid (2.3 mL, 51.1 mmol) was added dropwise under ice-cooling, and the mixture was stirred at 0° C. for 40 min. Water was added to the mixture, 4 mol/L aqueous sodium hydroxide solution was added dropwise to neutralize the mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-60/40 v/v) to give methyl 2-(2-methoxyacetamido)-3-nitrobenzoate (1.9 g, 51%).

후처리

  1. temperaturecooling
  2. additionwas added dropwise
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-60/40 v/v)

출처 및 근거

ORD 기록
ord-9cd116c4c1274faea0b7e4769178f31d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969345B2

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