Potassium Hydroxide → 3-(6,8-Dichloro-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)benzoic acid

HRID 1295435Notes

Reaction equation

HRID 1295435 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[C:17]([O:19]CC)=[O:18].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22386927HCID 22386927, compound2×

Product 1

HCID 223868523-(6,8-Dichloro-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)benzoic acidYield 55.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.3 g of ethyl 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzoate (intermediate 4) were dissolved in 60 ml of methanol and admixed with 60 ml of 2 N KOH. After two hours at 50° C., the mixture was concentrated in vacuo and the residue partitioned between water and ether. The water phase was adjusted to a pH of approx. 6 using 2 N HCl and the precipitate which formed was filtered off with suction. Drying afforded 1.7 g of the title compound as a colorless solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue partitioned between water and ether
  3. customthe precipitate which formed
  4. filtrationwas filtered off with suction
  5. customDrying

Sources & evidence

ORD record
ord-21bda20232d3408d9cceef1a6cbc49bb
Source dataset
uspto-grants-2007_07
Patent number
US07241775B2

Reaction notes

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