Nitric Acid → HCID 86721358、化合物

HRID 869528

反応式

HRID 869528 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 86721358HCID 86721358、化合物収率 51%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

[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%).

後処理

  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)

出典と根拠

ORDレコード
ord-9cd116c4c1274faea0b7e4769178f31d
出典データセット
uspto-grants-2015_03
特許番号
US08969345B2

関連ノート

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