Ethanol → HCID 11360072, compound

HRID 1406208Notes

Reaction equation

HRID 1406208 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-fe7ab105a9e448bd8caa0360a8165608
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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