Nitric Acid → Methyl 3-acetylamino-6-bromo-2-nitrobenzoate

HRID 1038463ノート

反応式

HRID 1038463 の反応式
S(=O)(=O)(O)O.[C:6]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([Br:20])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16])(=[O:8])[CH3:7].[N+:21]([O-])([OH:23])=[O:22]>O>[C:6]([NH:9][C:10]1[C:19]([N+:21]([O-:23])=[O:22])=[C:14]([C:13]([Br:20])=[CH:12][CH:11]=1)[C:15]([O:17][CH3:18])=[O:16])(=[O:8])[CH3:7]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 58891822Methyl 5-acetamido-2-bromobenzoate

生成物 1

HCID 11151255Methyl 3-acetylamino-6-bromo-2-nitrobenzoate収率 62%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To conc. sulfuric acid (150 mL), methyl 5-acetylamino-2-bromobenzoate (Reference Compound No. 1-(2), 18.5 g, 68.1 mmol) was added at 0° C. portionwise, and conc. nitric acid (150 mL) was added dropwise thereto over 1 hour. The reaction mixture was stirred for 30 minutes, poured into iced water (1 L), and then extracted with ethyl acetate (500 mL, 2 times). The organic layer was washed with water (1 L, 2 times), saturated aqueous sodium hydrogen carbonate solution (1 L), and saturated brine (1 L) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (13.4 g) as a yellow solid. (Yield 62%)

後処理

  1. addition1-(2), 18.5 g, 68.1 mmol) was added at 0° C. portionwise
  2. extractionextracted with ethyl acetate (500 mL, 2 times)
  3. washThe organic layer was washed with water (1 L, 2 times), saturated aqueous sodium hydrogen carbonate solution (1 L), and saturated brine (1 L) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-d8512153a50b4293b2d8c3dd8b6ba5c0
出典データセット
uspto-grants-2013_10
特許番号
US08551991B2

反応ノート

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