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

HRID 1385071ノート

反応式

HRID 1385071 の反応式
[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]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2 回HCID 5757772-Indancarboxylic Acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0ca3d5e2b90343759b6a94cf1818dc38
出典データセット
uspto-grants-2001_07
特許番号
US06262087B1

反応ノート

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