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

HRID 423746

反応式

HRID 423746 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].C(C1NC2C(C=1)=CC=CC=2)(C)(C)C.[N+:27]([O-])([O-:29])=[O:28].[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+:27]([O-:29])=[O:28])=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 5941662-tert-Butyl-1H-indoleHCID 46426432-(tert-Butyl)indoline

生成物 1

HCID 574701952-(tert-Butyl)-6-nitroindoline収率 32%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

To a solution of the mixture of 2-tert-butyl-2,3-dihydro-1H-indole and 2-tert-butyl-1H-indole (9.7 g ) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 55.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h, 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-nitro-2,3-dihydro-1H-indole (4.0 g, 32% over 2 steps).

後処理

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

出典と根拠

ORDレコード
ord-b6a05506104e43adbdfe0df4cafdb503
出典データセット
uspto-grants-2012_01
特許番号
US08101767B2

関連ノート

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