Potassium Hydroxide → HCID 11335766, compound

HRID 1866397Notes

Reaction equation

HRID 1866397 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][NH:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7].[OH-].[K+]>CCO>[C:18]1([C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[N:9][C:8]=2[C:6]([NH:5][CH2:4][C:3]([OH:24])=[O:2])=[O:7])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66713064HCID 66713064, compound

Product 1

HCID 11335766HCID 11335766, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of [(4-Phenyl-isoquinoline-3-carbonyl)-amino]-acetic acid methyl ester (144 mg, 0.45 mmol), KOH (325 mg, 5 mmol) and EtOH (10 ml) was stirred at ambient temperature for 18 h before the solvent was evaporated in vacuo. The residue was dissolved in water. The pH of the solution was adjusted to 3-4 by addition of concentrated aqueous HCl. The solution was then extracted with EtOAc (2×25 ml). The combined organic phases were dried over MgSO4 and concentrated in vacuo to give the title compound as a yellowish solid (127 mg); MS-(+)-ion: M+1=307.1.

Workup

  1. customwas evaporated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. additionThe pH of the solution was adjusted to 3-4 by addition of concentrated aqueous HCl
  4. extractionThe solution was then extracted with EtOAc (2×25 ml)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76dd761f6cad433ab72c59835bf5060b
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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