Methyl 2-(2-methoxyacetamido)-3-nitrobenzoate → methyl 2-(methoxymethyl)-1H-benzo[d]imidazole-4-carboxylate

HRID 869529Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=O>C(O)C.C(O)(=O)C>[CH3:1][O:2][CH2:3][C:4]1[NH:17][C:16]2[CH:15]=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]=2[N:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

[step 2] methyl 2-(2-methoxyacetamido)-3-nitrobenzoate (1.9 g, 6.9 mmol) obtained in step 1 was dissolved in a mixed solvent of ethanol (14 mL) and acetic acid (14 mL), reduced iron (2.3 g, 41.4 mmol) was added, and the mixture was stirred at 120° C. for 3 hr. After completion of the reaction, the mixture was filtered through celite. Saturated aqueous sodium hydrogen carbonate was added to the solution, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-20/80 v/v) to give methyl 2-(methoxymethyl)-1H-benzo[d]imidazole-4-carboxylate (1.1 g, 71%).

Workup

additionwas added
customAfter completion of the reaction
filtrationthe mixture was filtered through celite
additionSaturated aqueous sodium hydrogen carbonate was added to the solution
extractionthe mixture was extracted 3 times with ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-20/80 v/v)

Sources & evidence

ORD record: ord-f5e71b9bd12944d58504c6d6dc0ea70d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969345B2

Reaction notes

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