Nitric Acid → 6-Nitro-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 324357

Reaction equation

HRID 324357 reaction equation
[CH:1]1([C:10]([OH:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N+:13]([O-])([OH:15])=[O:14]>ClCCl.OS(O)(=O)=O>[N+:13]([C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH2:2][CH:1]2[C:10]([OH:12])=[O:11])=[CH:5][CH:6]=1)([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 857281H-Indene-1-carboxylic acid, 2,3-dihydro-

Product 1

HCID 123184886-Nitro-2,3-dihydro-1H-indene-1-carboxylic acidYield 112.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-indancarboxylic acid (30 g), prepared according to the method of Hansen et al. Helv. Chim. Acta 1982, 33, 325-343, in dichloromethane (50 ml) was mixed with concentrated sulphuric acid (300 ml) at −10° C. A mixture of 100% HNO3 (11.4 g) in concentrated H2SO4 (96 ml) was added dropwise under vigorous stirring below −10° C. After stirring for one hour at 10° C., the mixture was poured onto ice. Extraction with ethyl acetate (2×300 ml), drying (anh. MgSO4) and finally evaporation of the organic solvent afforded 42 g of the title compound. Mp 126-130° C.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring for one hour at 10° C.
  3. additionthe mixture was poured onto ice
  4. extractionExtraction with ethyl acetate (2×300 ml)
  5. customdrying
  6. custom(anh. MgSO4) and finally evaporation of the organic solvent

Sources & evidence

ORD record
ord-5f027fa960414911aac6162f707e6945
Source dataset
uspto-grants-2001_04
Patent number
US06218394B1

Linked notes

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