Hydrochloric Acid → Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

HRID 1480930Notes

Reaction equation

HRID 1480930 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:17][N:18]([CH2:29][C:30]([O:32][CH3:33])=[O:31])S(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+].CO.Cl>CS(C)=O.O>[CH3:33][O:32][C:30]([C:29]1[N:18]=[CH:17][C:5]2[C:4]([C:3]=1[OH:2])=[CH:9][CH:8]=[C:7]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:6]=2)=[O:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 89812990Methyl 2-((N-(2-methoxy-2-oxoethyl)-4-methylphenylsulfonamido)methyl)-4-phenoxybenzoate

Product 1

HCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixture of 2-{[Methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-4-phenoxy-benzoic acid methyl ester (14.0 g, 28.1 mmol) in DMSO (56 mL) was slowly added 30% NaOMe in MeOH (15.3 mL, 84.3 mmol). The resultant mixture was stirred at room temperature for 30 min and poured into 200 mL of ice and water. It was slowly acidified by conc. HCl aq. solution (10 mL) and then extracted with EtOAc. Organic layer was washed with 3% NaHCO3 solution, water and brine, and was dried over Na2SO4, filtered and concentrated. Crude produce was purified by silica gel chromatography to provide the title compound 6.05 g (20.5 mmol) in 72.9% yield. 1H NMR in CDCl3, δ in ppm: 11.7 (s, 1H), 8.59 (s, 1H), 8.36 (d, 1H, J=9.2 Hz), 7.55-7.1 (m, 7H), 4.07 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washOrganic layer was washed with 3% NaHCO3 solution, water and brine
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customCrude produce
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-0de0cbd92e1e4be899562d87addf418e
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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