Ethanol → HCID 11360072, compound

HRID 908822Notes

Reaction equation

HRID 908822 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][NH:5][C:6]([C:8]1[N:9]=[C:10](Cl)[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+].[CH3:28][CH2:29][OH:30]>>[CH2:29]([O:30][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:2])=[O:25])=[O:7])[N:9]=1)[CH3:28]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 86014604HCID 86014604, compound

Product 1

HCID 11360072HCID 11360072, compound

Procedure

A mixture of [(1-Chloro-4-phenyl-isoquinoline-3-carbonyl)-amino]-acetic acid methyl ester (177 mg, 0.5 mmol), KOH (325 mg, 5 mmol) and EtOH (10 ml) was stirred at ambient temperature for 90 min before the solvent was evaporated in vacuo. The residue was dissolved in water (10 ml). The solution was acidified by addition of concentrated aqueous HCl and extracted with EtOAc (2×15 ml). The combined organic phases were dried over MgSO4 and concentrated in vacuo to give the title compound as a slightly yellowish solid (169 mg); MS-(+)-ion: M+1=351.0.

Workup

  1. customwas evaporated in vacuo
  2. dissolutionThe residue was dissolved in water (10 ml)
  3. additionThe solution was acidified by addition of concentrated aqueous HCl
  4. extractionextracted with EtOAc (2×15 ml)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e69488a661e54aa69545a3b21f5ee01f
Source dataset
uspto-grants-2011_09
Patent number
US08017625B2

Reaction notes

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