Hydrochloric Acid → HCID 20242564, compound

HRID 483149Notes

Reaction equation

HRID 483149 reaction equation
[ClH:1].Cl.[C:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][C:14]([N:22]([CH3:24])[CH3:23])=[N:13]2)=[CH:8][CH:7]=1)([OH:5])=[O:4].[CH3:25]O>>[ClH:1].[C:3]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][C:14]([N:22]([CH3:24])[CH3:23])=[N:13]2)=[CH:10][CH:11]=1)([O:5][CH3:25])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 20242570HCID 20242570, compound

Product 1

HCID 20242564HCID 20242564, compound

Procedure

The basic aqueous solution from the above experiment was made acidic with 5N hydrochloric acid, and evaporated to dryness to leave a white solid, containing 1-(4-carboxyphenyl)-1,4-dihydro-3-dimethylaminoisoquinoline hydrochloride. The crude acid was suspended in methanol (100 ml) and ethereal hydrogen chloride (2 ml) at room temperature for 16 h. The suspension was filtered and the filtrate was evaporated under reduced pressure. The residue was dissolved in dilute hydrochloric acid, washed with ethyl acetate, then basified with 10% sodium hydroxide solution and extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4) and ethereal HCl was added. The solvent was removed under reduced pressure and the residual solid was recrystallised from dichloroethane/ethyl acetate to give 1-(4-carbomethoxyphenyl)-1,4-dihydro-3-dimethylamino-isoquinoline hydrochloride as a pale yellow powder, m.p. 187°-193° C.

Workup

  1. customevaporated to dryness
  2. customto leave a white solid
  3. filtrationThe suspension was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in dilute hydrochloric acid
  6. washwashed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. washThe extracts were washed with brine
  9. dry with materialdried (MgSO4) and ethereal HCl
  10. additionwas added
  11. customThe solvent was removed under reduced pressure
  12. customthe residual solid was recrystallised from dichloroethane/ethyl acetate

Sources & evidence

ORD record
ord-469b44633651455d990d9cc54e488491
Source dataset
uspto-grants-1986_03
Patent number
US04578393

Reaction notes

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