Ammonia → HCID 53932883, compound

HRID 1680277Notes

Reaction equation

HRID 1680277 reaction equation
[NH3:1].[C:2]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[O:19]C(=O)C)[CH:15]([C:23](Cl)=[O:24])[CH2:14][CH2:13]2)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1C=CC=CC=1>[C:2]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[OH:19])[CH:15]([C:23]([NH2:1])=[O:24])[CH2:14][CH2:13]2)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54201713HCID 54201713, compound

Product 1

HCID 53932883HCID 53932883, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Dry ammonia is passed into a solution of 27 g of crude 5-benzoyl-6-acetoxy-indane-1-carboxylic acid chloride in 200 ml of anhydrous benzene at a temperature of 15°-20° C., with exclusion of moisture, until saturation is reached. The reaction solution is then evaporated to dryness in vacuo and the evaporation residue is partitioned between 200 ml of water and 3 times 200 ml of methylene chloride. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo. Fractional crystallisation of the evaporation residue from hot dimethylformamide-water gives 5-benzoyl-6-hydroxy-indane-1-carboxylic acid amide of melting point 205°-207° C. The starting material can be obtained as follows. A solution of 20 g of 5-benzoyl-6-hydroxy-indane-1-carboxylic acid in 200 ml of acetic anhydride is heated to the reflux temperature for 4 hours. It is then evaporated to dryness in vacuo, 50 ml of toluene are added to the evaporation residue and the mixture is evaporated to dryness. This procedure is repeated twice more. The crude 5-benzoyl-6-acetoxy-indane-1-carboxylic acid thus obtained is used directly for further conversion.

Workup

  1. customThe reaction solution is then evaporated to dryness in vacuo
  2. customthe evaporation residue is partitioned between 200 ml of water and 3 times 200 ml of methylene chloride
  3. washThe organic phases are washed until neutral,
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo
  6. customFractional crystallisation of the evaporation residue from hot dimethylformamide-water

Sources & evidence

ORD record
ord-1bcd85f4d4f64c97b3b6b43af3185ef4
Source dataset
uspto-grants-1981_06
Patent number
US04272547

Reaction notes

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