Methanol → Methyl 4-amino-2-fluoro-5-nitrobenzoate

HRID 470360Notes

Reaction equation

HRID 470360 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([F:19])[CH:8]=1.[CH3:20]O>>[NH2:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]([C:11]([O:13][CH3:20])=[O:12])=[C:9]([F:19])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 597853374-Amino-2-fluoro-5-nitrobenzoic acid

Product 1

HCID 53419670Methyl 4-amino-2-fluoro-5-nitrobenzoateYield 69%

Procedure

Sulfuric acid (10 mL) was added to a solution of 4-amino-2-fluoro-5-nitrobenzoic acid ammoniate (10 g, 46 mmol) in methanol (100 mL) and refluxed for 30 h. The solution was cooled to ambient temperature and the solid thus obtained was collected by filtration, washed with hexanes, and dried in vacuo at 40° C. for 14 h to afford the desired methyl 4-amino-2-fluoro-5-nitrobenzoate as a yellow solid (6.84 g, 31.9 mmol, 69%). 1H NMR (MeOD) δ 8.62-8.58 (m, 1H), 6.63-6.59 (m, 1H).

Workup

  1. temperaturerefluxed for 30 h
  2. customthe solid thus obtained
  3. filtrationwas collected by filtration
  4. washwashed with hexanes
  5. customdried in vacuo at 40° C. for 14 h

Sources & evidence

ORD record
ord-4f3c42fec1894629a3d54dc0ae4bc438
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

Loading…