Nitric Acid → 5-Nitro-2,3-dihydro-1H-indene-2-carboxylic acid

HRID 1385071노트

반응식

HRID 1385071 반응식
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>CCOCC>[N+:18]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3]2)([O-:20])=[O:19]

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2회HCID 5757772-Indancarboxylic Acid

생성물 1

HCID 185458885-Nitro-2,3-dihydro-1H-indene-2-carboxylic acid

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
5 °C

실험 절차

A solution of indane-2-carboxylic Acid 9a (18.8 g) in ether (250 ml) was added to conc. sulfuric acid (300 ml) (temp.=3-13° C.). To this mixture, a solution of conc. nitric acid (4.4 ml) and conc. sulfuric acid (100 ml) was added (temp.=−1° C.). The mixture was stirred at 2-8° C. for 1 h, poured onto ice, and the aqueous phase was extracted with ether. The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to dryness in vacuo. The residue was crystallized from ether to give 5-nitroindane-2-carboxylic acid (6.0 g). The solid was dissolved in CH2Cl2 (100 ml) and DMF (1 ml). Thionyl chloride (8.4 ml) was added, and the solution was boiled under reflux for 5 hours. Evaporation in vacuo gave the title compound (8.6 g).

후처리

  1. additionpoured onto ice
  2. extractionthe aqueous phase was extracted with ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness in vacuo
  6. customThe residue was crystallized from ether

출처 및 근거

ORD 기록
ord-0ca3d5e2b90343759b6a94cf1818dc38
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262087B1

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