Ethyl Acetate → Indane

HRID 36926

Reaction equation

HRID 36926 reaction equation
ClC1C=CC=CC=1C(Cl)=O.N[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][CH2:16][CH2:15]2.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O>[CH2:17]1[C:18]2[C:14](=[CH:13][CH:12]=[CH:20][CH:19]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 691102-Chlorobenzoyl chlorideHCID 90496Indan-5-amine

Product 1

HCID 10326Indane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chlorobenzoyl chloride (11.8 g) was added dropwise to a stirred mixture of 5-aminoindan (9.0 g), potassium carbonate (9.3 g), ethyl acetate (90 ml) and water (90 ml) under ice-cooling. The mixture was further stirred under ice-cooling for one hour, at the end of which time the organic layer was separated, washed with water, dried (MgSO4) and distilled to remove the solvent. The procedure gave crystals of 5-2-chlorobenzoylamino)indan. The crystals were collected by filtration and recrystallized from isopropyl ether to give colorless needles, m.p. 144°-145° C.

Workup

  1. temperaturecooling
  2. temperaturecooling for one hour, at the end of which time the organic layer
  3. customwas separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. distillationdistilled
  7. customto remove the solvent

Sources & evidence

ORD record
ord-88d69e93a5f6475badf02e8876958cbe
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Linked notes

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