Sodium Methoxide → Methyl 4-hydroxy-8-iodoisoquinoline-3-carboxylate
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:5]=1[CH2:11][N:12]([CH2:23][C:24]([O:26][CH3:27])=[O:25])S(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>CO>[CH3:27][O:26][C:24]([C:23]1[N:12]=[CH:11][C:5]2[C:4]([C:3]=1[OH:2])=[CH:9][CH:8]=[CH:7][C:6]=2[I:10])=[O:25]Participants
4
Procedure
To a solution of crude 3-Iodo-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid methyl ester (37.8 g) in methanol (220 mL) was added a solution of NaOMe (30 wt %) in methanol (40 mL) with stirring. After stirring for 18 h at ambient temperature the mixture was concentrated in vacuo. To the residue was added 1 N hydrochloric acid (200 mL) and the mixture was extracted with hot ethyl acetate (1×300 mL). The organic phase was then washed with concentrated aqueous NaHCO3 solution (3×200 mL), dried over MgSO4 and concentrated in vacuo. The residue was recrystallized from ethyl acetate to give the title compound as a tan solid (10.1 g); MS-(+)-ion: M+1=329.8.
Workup
- stirringAfter stirring for 18 h at ambient temperature the mixture
- concentrationwas concentrated in vacuo
- additionTo the residue was added 1 N hydrochloric acid (200 mL)
- extractionthe mixture was extracted with hot ethyl acetate (1×300 mL)
- washThe organic phase was then washed with concentrated aqueous NaHCO3 solution (3×200 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-9f83905c1b5c4c949564b33e407c4906
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174976B2
Reaction notes
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