Chloride → Methyl 4-amino-3-nitrobenzoate

HRID 59803

Reaction equation

HRID 59803 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Cl-].[CH3:15]O>>[CH3:15][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

4

Reactant 3

HCID 312ChlorideHCID 887MethanolHCID 74115Benzoic acid, 4-amino-3-nitro-

Product 1

HCID 3941008Methyl 4-amino-3-nitrobenzoateYield 81%

Procedure

To a mixture of 4-amino-3-nitro-benzoic acid (10.0 g, 54.9 mmol) suspended in methanol (150 mL) was added thiony chloride (3.99 mL, 54.9 mmol). The mixture was heated to reflux overnight, then cooled to room temperature and filtered. The solid recovered by filtration was rinsed with cold methanol and dried to give 8.68 g (81%) of 4-amino-3-nitro-benzoic acid methyl ester.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. filtrationThe solid recovered by filtration
  5. washwas rinsed with cold methanol
  6. customdried

Sources & evidence

ORD record
ord-672a1d09152b4116b8e1310c6d95a876
Source dataset
uspto-grants-2016_09
Patent number
US09440956B2

Linked notes

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