Methanol → HCID 89812934, compound

HRID 1481201Notes

Reaction equation

HRID 1481201 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[C:19]([NH:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:20].S(=O)(=O)(O)O.[CH3:33]O>>[CH3:33][O:26][C:25](=[O:27])[CH2:24][CH2:23][CH2:22][NH:21][C:19]([C:3]1[N:4]=[CH:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[C:8]([O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:7]=2)=[O:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 71735139HCID 71735139, compound

Product 1

HCID 89812934HCID 89812934, compound

Procedure

To a solution of 4-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-butyric acid (1.32 g, 3.6 mmol) in MeOH (7.2 mL) was added 10% sulfuric acid. The reaction mixture was stirred at reflux for 20 hours. After cooled to rt, the solvent was concentrated in vacuo as a oil and purified by silica gel chromatography over silica gel, eluting with 15-75% EtOAc/hexanes to give product (900 mg) as a colorless oil: MS (m/z) 381.0 (M+1)+.

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationthe solvent was concentrated in vacuo as a oil
  3. custompurified by silica gel chromatography over silica gel
  4. washeluting with 15-75% EtOAc/hexanes

Sources & evidence

ORD record
ord-dc7cb1a951794befa57f9bcd8cedd929
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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