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

HRID 1668919Notes

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-dd1386327b91425fa104254cf0985e24
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989461B2

Reaction notes

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