Sodium Carbonate → 2-(tert-Butyl)-6-nitroindoline

HRID 468393

反応式

HRID 468393 の反応式
[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:3])[CH3:2].[N+:14]([O-])([O-:16])=[O:15].[K+].C([O-])([O-])=O.[Na+].[Na+]>OS(O)(=O)=O>[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 46426432-(tert-Butyl)indoline

生成物 1

HCID 574701952-(tert-Butyl)-6-nitroindoline収率 32.8%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

To a solution of 2-tert-butylindoline (9.7 g) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 56 mmol) at 0° C. After addition, the reaction mixture was stirred at room temperature for 1 h. The mixture was carefully poured into cracked ice, basified with Na2CO3 to pH 8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitroindoline (4.0 g, 31% over two steps). 1H NMR (300 MHz, CDCl3) δ 7.52 (dd, J=1.8, 8.1 Hz, 1H), 7.30 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 3.76 (t, J=9.6 Hz, 1H), 2.98-3.07 (m, 1H), 2.82-2.91 (m, 1H), 0.91 (s, 9H).

後処理

  1. customat 0° C
  2. additionAfter addition
  3. additionThe mixture was carefully poured into cracked ice
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-ebca98e539db4207bbe2e84b5b25250e
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

関連ノート

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