HCID 10655655, compound → HCID 20095725, compound

HRID 1770291Notes

Reaction equation

HRID 1770291 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[C:10]1(=[O:24])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][C:11]21[CH2:23][CH2:22][CH2:21][CH2:20]2>S(=O)(=O)(O)O>[N+:6]([C:17]1[CH:18]=[C:19]2[C:14]([CH2:13][CH2:12][C:11]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:10]2=[O:24])=[CH:15][CH:16]=1)([O-:9])=[O:7]

Participants

4

Reactant 2

HCID 10655655HCID 10655655, compoundHCID 71777668Sulfuric acid, mixt. with nitric acid

Product 1

HCID 20095725HCID 20095725, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

41.1.14 ml of a sulphuric acid/nitric acid 65% 1:1 mixture was slowly added dropwise to a solution of 20 g of 3'4'-dihydro-spiro[cyclopentane-1,2'(1'H)-naphthalen]-1'-one in 60 ml of sulphuric acid. After stirring for 2 hrs. at RT the mixture was poured on to 200 g of ice, extracted with ether, washed with a saturated aqueous NaHCO3 solution and with water, dried on Na2SO4, filtered, concentrated and chromatographed over silica gel with cyclohexane/ethyl acetate 9:1. Yield: 12.7 g (52%). A sample was recrystallized from hot isopropyl ether and gave 7'-nitro-3'4'-dihydro-spiro[cyclopentane-1,2'(1'H)-naphthalen]-1'-one as white crystals; m.p. 69°-70° C.

Workup

  1. extractionextracted with ether
  2. washwashed with a saturated aqueous NaHCO3 solution and with water
  3. customdried on Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed over silica gel with cyclohexane/ethyl acetate 9:1
  7. customA sample was recrystallized from hot isopropyl ether

Sources & evidence

ORD record
ord-a5257c16d044409190a6a6b20fc8aa47
Source dataset
uspto-grants-1995_01
Patent number
US05385947

Reaction notes

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