Nitric Acid → 5-Nitro-2,3-dihydro-1H-indene-2-carboxylic acid
Reaction equation
[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]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
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).
Workup
- additionpoured onto ice
- extractionthe aqueous phase was extracted with ether
- washThe combined organic extracts were washed with brine
- dry with materialdried (MgSO4)
- customevaporated to dryness in vacuo
- customThe residue was crystallized from ether
Sources & evidence
- ORD record
- ord-0ca3d5e2b90343759b6a94cf1818dc38
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06262087B1
Reaction notes
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