Acetone → 6-Benzoyl-2,3-dihydro-1H-indene-1-carboxamide

HRID 436179Notes

Reaction equation

HRID 436179 reaction equation
CC(C)=[O:3].[CH2:5]([C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][CH2:17][CH:18]2[C:21]([NH2:23])=[O:22])=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O>O>[C:5]([C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][CH2:17][CH:18]2[C:21]([NH2:23])=[O:22])=[CH:14][CH:13]=1)(=[O:3])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 25408Sodium DichromateHCID 20310092HCID 20310092, compound

Product 1

HCID 123185126-Benzoyl-2,3-dihydro-1H-indene-1-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 150 ml. of acetone is added 12.5 g. of 6-benzylindan-1-carboxamide, followed by the dropwise addition of a solution of 5 g. of sodium dichromate in 24 ml. of 6N sulfuric acid. After the addition has been completed, the mixture is stirred overnight. Then 200 ml. of water is added and the acetone is distilled off under reduced pressure. The residue is extracted with ethyl acetate. The extract is washed with water and dried, followed by removal of the solvent by distillation under reduced pressure. The residue is purified by column chromatography (500 g. of silica gel; eluted with a 7:3 solvent mixture of chloroform and acetone) and the resultant crude crystals are recrystallized from benzene. The procedure gives 6-benzoylindan-1-carboxamide as crystals melting at 195°-197° C.

Workup

  1. additionAfter the addition
  2. distillationthe acetone is distilled off under reduced pressure
  3. extractionThe residue is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. customfollowed by removal of the solvent by distillation under reduced pressure
  7. customThe residue is purified by column chromatography (500 g
  8. washeluted with a 7:3 solvent mixture of chloroform and acetone) and the resultant crude crystals
  9. customare recrystallized from benzene

Sources & evidence

ORD record
ord-fe13e02733f34bd6951e58e0d0573772
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

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