Methanol → Methyl 2-amino-3-nitrobenzoate

HRID 520443Notes

Reaction equation

HRID 520443 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:19]O>>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2196332-Amino-3-nitrobenzoic acid

Product 1

HCID 607264Methyl 2-amino-3-nitrobenzoateYield 95%

Conditions

Temperature
100 °C

Procedure

2-amino-3-nitrobenzoic acid 1 (5 g, 27.4 mmol) was dissolved in methanol (100 mL) and con H2SO4 was added. The mixture was heated at 100° C. for 12 h, concentrated to dryness and suspended in H2O (50 mL). The mixture was extracted with CH2Cl2 (50 mL), dried (MgSO4) and concentrated. The crude residue was purified by flash chromatography to give 11 (5.1 g, 95% yield).

Workup

  1. concentrationconcentrated to dryness
  2. extractionThe mixture was extracted with CH2Cl2 (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9cae87eb11874fe79f3aa8e1580c1c65
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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