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

HRID 1072530Notes

Reaction equation

HRID 1072530 reaction equation
C([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]2[C:20]3[C:15](=[C:16]([Cl:22])[CH:17]=[C:18]([Cl:21])[CH:19]=3)[CH2:14][N:13]([CH3:23])[CH2:12]2)[CH:6]=1)C.[OH-].[K+]>CO>[Cl:21][C:18]1[CH:19]=[C:20]2[C:15](=[C:16]([Cl:22])[CH:17]=1)[CH2:14][N:13]([CH3:23])[CH2:12][CH:11]2[C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:24])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22386927HCID 22386927, compound

Product 1

HCID 223868523-(6,8-Dichloro-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)benzoic acidYield 65.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

500 mg 3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinoline-4-yl)-benzoic-acid-ethyl-ester (Example 220) were dissolved in 15 ml methanol and treated with 10 ml of a 2 N KOH-solution. After 1 h at 50° C. the solvent was removed i. vac. The residue was taken up in water and was washed with ether. The aqueous phase was seperated and 2 N HCl was added until a pH-value of about 6 was reached. The precipitate was filtered off by suction and dried to give 304 mg of the title compound.

Workup

  1. customAfter 1 h at 50° C. the solvent was removed i
  2. washwas washed with ether
  3. customThe aqueous phase was seperated
  4. addition2 N HCl was added until a pH-value of about 6
  5. filtrationThe precipitate was filtered off by suction
  6. customdried

Sources & evidence

ORD record
ord-a0457b285a694cc6a828f8c6f1a7f261
Source dataset
uspto-grants-2005_06
Patent number
US06911453B2

Reaction notes

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