Diethyl Ether → Hydrogen maleate

HRID 616345Notes

Reaction equation

HRID 616345 reaction equation
[CH:1]([N:4]1[CH2:8][CH:7]([CH2:9][O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[CH:14]=[CH:13][N:12]=2)[O:6]C1C1C=CC=CC=1)([CH3:3])[CH3:2].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].CCOCC>Cl.CO>[OH:6][CH:7]([CH2:8][NH:4][CH:1]([CH3:3])[CH3:2])[CH2:9][O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[CH:14]=[CH:13][N:12]=1.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([O-:34])=[O:33]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 444266Maleic AcidHCID 203698011-(3-Isopropyl-2-phenyl-5-oxazolidinylmethoxy)-7-methoxyisoquinoline

Product 2

HCID 11966254Hydrogen maleateHCID 203697941-(2-Hydroxy-3-isopropylaminopropoxy)-7-methoxyisoquinoline

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

1 g of 1-(3-isopropyl-2-phenyl-5-oxazolidinylmethoxy)-7-methoxy-isoquinoline is heated to 80° in 10 cc of 1 N hydrochloric acid for 10 minutes. The reaction mixture is extracted with ether. The ethereal phase is discarded, and the aqueous phase is made alkaline with potash, extracted with ether, the ether phase is dried over magnesium sulphate and concentrated, whereby a crystalline product is obtained which is treated in methanol with maleic acid. Ether is added, whereby 1-(2-hydroxy-3-isopropylaminopropoxy)-7-methoxyisoquinoline is obtained as hydrogen maleate. M.P. 144°-146°.

Workup

  1. extractionThe reaction mixture is extracted with ether
  2. extractionextracted with ether
  3. dry with materialthe ether phase is dried over magnesium sulphate
  4. concentrationconcentrated
  5. customwhereby a crystalline product is obtained which

Sources & evidence

ORD record
ord-82a2a7a4b92e470e809f317db19c9646
Source dataset
uspto-grants-1978_02
Patent number
US04073909

Reaction notes

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