Methyl 2-[(2-methoxyethoxy)methoxy]-3-(5-methoxypyridin-2-ylamino)benzoate → Methyl-2-hydroxy-3-(5-methoxypyridin-2-ylamino)benzoate

HRID 912431Notes

Reaction equation

COCCOC[O:7][C:8]1[C:17]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][N:20]=2)=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]>CO>[CH3:13][O:12][C:10](=[O:11])[C:9]1[CH:14]=[CH:15][CH:16]=[C:17]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][N:20]=2)[C:8]=1[OH:7]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of methyl 2-[(2-methoxyethoxy)methoxy]-3-(5-methoxypyridin-2-ylamino)benzoate 1.0 g (2.8 mmol) of step 3 in methanol 20 mL was added 6NHCl 2 mL, followed by stirring at 40° C. for 30 min. The reaction mixture was cooled to room temperature, concentrated in a vacuum, diluted with ethylacetate, washed with distilled water, and a saturated NaCl solution. After drying over magnesium sulfate and concentration in a vacuum, purification by column chromatography (developing solvent: ethylacetate/hexane=1/2) afforded 0.70 g of the title compound (yield 90%).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in a vacuum
additiondiluted with ethylacetate
washwashed with distilled water
dry with materialAfter drying over magnesium sulfate and concentration in a vacuum, purification by column chromatography (developing solvent: ethylacetate/hexane=1/2)

Sources & evidence

ORD record: ord-a95e4aae34fc43d6b0bfc6872a39ac81
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026235B1

Reaction notes

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