Acetic Acid → 1-Acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethyl-7-nitroindoline

HRID 1531974ノート

反応式

HRID 1531974 の反応式
S(=O)(=O)(O)[OH:2].[N+:6]([O-:9])(O)=[O:7].[C:10]([N:13]1[C:21]2[C:16](=[C:17]([CH3:24])[C:18]([Br:23])=[C:19]([CH3:22])[CH:20]=2)[CH:15]([CH2:25][C:26](=[C:30]=[O:31])OCC)[CH2:14]1)(=[O:12])[CH3:11].[CH3:32][C:33](O)=O>>[C:10]([N:13]1[C:21]2[C:16](=[C:17]([CH3:24])[C:18]([Br:23])=[C:19]([CH3:22])[C:20]=2[N+:6]([O-:9])=[O:7])[CH:15]([CH2:25][CH2:26][C:30]([O:31][CH2:32][CH3:33])=[O:2])[CH2:14]1)(=[O:12])[CH3:11]

参加物

5

反応物 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 867565351-Acetyl-5-bromo-3-(2-ethoxy-carbonylethyl)-4,6-dimethylindoline

生成物 1

HCID 222473011-Acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethyl-7-nitroindoline

実験手順

To a mixture of AcOH (10 ml), conc. sulfuric acid (10 ml) and nitric acid (0.55 ml) was added by portions 1-acetyl-5-bromo-3-(2-ethoxy-carbonylethyl)-4,6-dimethylindoline (3.0 g) at 0° C., and the mixture was stirred at the same temperature for 5 hr. The reaction mixture was poured into ice water and extracted with CHCl3 (100 ml). After washing with water, the mixture was dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=50/1−10/1) to give 2.7 g of 1-acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethyl-7-nitroindoline.

後処理

  1. extractionextracted with CHCl3 (100 ml)
  2. washAfter washing with water
  3. dry with materialthe mixture was dried over anhydrous sodium sulfate
  4. customCHCl3 was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=50/1−10/1)

出典と根拠

ORDレコード
ord-2b96d873fb67480bb4f40c60b4cb51f5
出典データセット
uspto-grants-2001_03
特許番号
US06200988B1

反応ノート

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