Sodium Carbonate → 4-[2-Oxo-2-(1,2,3,4-tetrahydro-2-isoquinolinyl)ethoxy]-alpha-oxobenzeneacetic acid

HRID 2225814Notes

Reaction equation

HRID 2225814 reaction equation
C([O:3][C:4](=[O:27])[C:5](=[O:26])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14](=[O:25])[N:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16]2)=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[O:25]=[C:14]([N:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)[CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([C:5](=[O:26])[C:4]([OH:27])=[O:3])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 537619884-[2-Oxo-2-(1,2,3,4-tetrahydro-2-isoquinolinyl)ethoxy]-alpha-oxobenzeneacetic acid ethyl ester

Product 1

HCID 190043154-[2-Oxo-2-(1,2,3,4-tetrahydro-2-isoquinolinyl)ethoxy]-alpha-oxobenzeneacetic acidYield 28.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-[2-Oxo-2-(1,2,3,4-tetrahydro-2-isoquinolinyl)ethoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.3 g) in methanol (10 mL) was treated with sodium carbonate (0.113 g) in water (3 mL), and the mixture was stirred at room temperature for 20 minutes. After the solvents were removed in vacuo, water (10 mL) was added and the solution acidified with 3N hydrochloric acid, then the aqueous layer was extracted with dichloromethane-tetrahydrofuran (1:1). The organic layer was dried (MgSO4), evaporated and the residual solid was crystallized from acetone-tetrahydrofuran-hexane to yield 0.078 g of 4-[2-oxo-2-(1,2,3,4-tetrahydro-2-isoquinolinyl)ethoxy]-alpha-oxobenzeneacetic acid, mp 218°-220° C.

Workup

  1. customAfter the solvents were removed in vacuo, water (10 mL)
  2. additionwas added
  3. extractionthe aqueous layer was extracted with dichloromethane-tetrahydrofuran (1:1)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customthe residual solid was crystallized from acetone-tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-55fc310706834f61af80ccfef5e01f4b
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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