Hydrochloric Acid → HCID 54533235, compound

HRID 1679077Notes

Reaction equation

HRID 1679077 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24]C(C2OCCO2)C)[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2].[O:32]1CCO[CH2:34][CH2:33]1.Cl>O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24][C:33](=[O:32])[CH3:34])[C:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 53722379HCID 53722379, compound

Product 1

HCID 54533235HCID 54533235, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 8 g. of 5-chloro-2-[4-(1,3-dioxolan-2-yl)pentyl]-3-phenylisoindole-1-carboxylic acid ethyl ester in a mixture of 40 ml. of dioxane and 10 ml. of water is treated with 2 ml. of concentrated hydrochloric acid and then boiled at reflux for 3 hours. The solution obtained is concentrated to dryness under reduced pressure and the residue partitioned between water and methylene chloride. The organic phase is washed with a 2-N sodium carbonate solution and then with a saturated aqueous sodium chloride solution. After drying over sodium sulfate, the solvent is removed, and there is obtained 5-chloro-2-(4-oxopentyl)-3-phenylisoindole-1-carboxylic acid ethyl ester having a melting point of 93°-94° C. Crystallization from ether/hexane yields colorless crystals; melting point 94°-95° C.

Workup

  1. additionA suspension of 8 g
  2. temperatureat reflux for 3 hours
  3. customThe solution obtained
  4. concentrationis concentrated to dryness under reduced pressure
  5. customthe residue partitioned between water and methylene chloride
  6. washThe organic phase is washed with a 2-N sodium carbonate solution
  7. dry with materialAfter drying over sodium sulfate
  8. customthe solvent is removed

Sources & evidence

ORD record
ord-a90f67952b05465ebfb2868cd4c21041
Source dataset
uspto-grants-1978_03
Patent number
US04077978

Reaction notes

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