Methanol → Methyl 4-amino-3-nitrobenzoate

HRID 446224

Reaction equation

HRID 446224 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].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][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 887MethanolHCID 24386Thionyl ChlorideHCID 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 mm0l) suspended in methanol (150 mL) was added thionyl 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-082a2ee6ac3344899b1513bf4c1150ff
Source dataset
uspto-grants-2013_07
Patent number
US08476457B2

Linked notes

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