Hydrochloric Acid → 3-Amino-4-methyl-2-nitrobenzoic acid

HRID 2092277Notes

Reaction equation

C([NH:4][C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9])(=O)C.Cl>O1CCOCC1>[NH2:4][C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Acetamido-4-methyl-2-nitrobenzoic acid (65 g, 273 mmol) was taken in dioxane (350 mL) and treated with 5 N aqueous HCl (150 mL). The reaction was stirred at 80° C. for 16 h. The dioxane was removed under reduced pressure and the residue poured onto crushed ice. The resulting precipitate was filtered off. The filtrate was extracted with ethyl acetate (2×). The organic layer and the solid were combined and concentrated under vacuum to give 3-amino-4-methyl-2-nitrobenzoic acid (45 g, 84% yield) as a yellow solid. MS (M+H)+ 197.

Workup

customThe dioxane was removed under reduced pressure
additionthe residue poured
customonto crushed ice
filtrationThe resulting precipitate was filtered off
extractionThe filtrate was extracted with ethyl acetate (2×)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-a6c5cc26b0bb4acea86595fc00af01f3
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440674B2

Reaction notes

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