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

HRID 73919

반응식

HRID 73919 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 574701952-(tert-Butyl)-6-nitroindoline수율 32%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d209ee55a7144c0491fdf3d3288c2560
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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