Ethyl Acetate → 2-chloro-N-(2,3-dihydro-1H-inden-5-yl)benzamide

HRID 258034Notes

Reaction equation

HRID 258034 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][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>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][CH2:16][CH2:15]2)=[O:5]

Participants

6

Reactant 4

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

Product 1

HCID 7699162-chloro-N-(2,3-dihydro-1H-inden-5-yl)benzamide

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-8dec3a5890954991a41d6f8ae9652801
Source dataset
uspto-grants-1993_11
Patent number
US05264454

Reaction notes

Loading…