Hydrochloric Acid → HCID 19696488, compound

HRID 863456Notes

Reaction equation

HRID 863456 reaction equation
C([Li])CCC.Br[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][N:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:11]2.CN(C)[CH:24]=[O:25].Cl>CCCCCC.CCOCC>[C:16]1([N:10]2[CH2:9][C:8]3[C:7]([CH:24]=[O:25])=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:11]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 19696473HCID 19696473, compoundHCID 178418339Butyllithium

Product 1

HCID 19696488HCID 19696488, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent4×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

2.3 ml (3.7 mmol) of a 1.6 molar solution of butyllithium in hexane are added to 14 ml of dry ether in a dry apparatus under argon. A solution of 930 mg (3.4 mmol) of 4-bromo-2-phenylisoindoline in 10 ml of dry ether is then added dropwise at -70° C. The mixture is stirred at -70° C. for 30 minutes, and 0.3 ml of dry dimethylformamide in 0.5 ml of ether is added. The mixture is stirred at 70° C. for 3 hours and heated to -5° C., and 13.6 ml of 1N hydrochloric acid are added dropwise. 50 ml of ether are added and the mixture is separated. The aqueous phase is extracted by shaking with ether and the combined ether phases are washed once with water, dried and concentrated. 600 mg of yellowish crystals of melting point 120°-122° C. are obtained.

Workup

  1. stirringThe mixture is stirred at 70° C. for 3 hours
  2. temperatureheated to -5° C.
  3. customthe mixture is separated
  4. extractionThe aqueous phase is extracted
  5. stirringby shaking with ether
  6. washthe combined ether phases are washed once with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f0e5eb04b1fc4ee394cd261d0c25f458
Source dataset
uspto-grants-1998_02
Patent number
US05721248

Reaction notes

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