Hydrochloric Acid → 4-Hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl ester

HRID 1481112Notes

Reaction equation

HRID 1481112 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.C[O-].[Na+].CO.Cl>CN(C=O)C.O>[CH3:1][O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH:12]=2)=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23694274Sodium methanolate methanolHCID 667126187-(4-Methoxy-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 898128354-Hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid methyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-hydroxy-7-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid butyl ester (prepared according to U.S. Pat. No. 7,928,120) (20 mg, 0.054 mmol) in DMF (0.5 mL) was added 0.5 M NaOMe/MeOH (0.32 mL, 0.16 mmol). The resultant mixture was microwaved at 80° C. for 1.5 h. Reaction mixture was diluted with water (70 mL) and acidified by 1 N HCl to pH=4. Precipitate was collected and dried in vacuo to provide the title compound 15 mg (0.046 mmol) in 85% yield. LC-MS ESI+: 326.10 (M+1)+.

Workup

  1. customprepared
  2. customReaction mixture
  3. customPrecipitate was collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-97af080638c941cda5e3d65001748358
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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