Stannous Chloride → 2-amino-5-fluoro-3-methylbenzoic acid

HRID 61267Notes

Reaction equation

HRID 61267 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:11][C:5]1[C:4]([CH3:14])=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 534307765-Fluoro-3-methyl-2-nitrobenzoic acid

Product 1

HCID 289741642-amino-5-fluoro-3-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-fluoro-3-methyl-2-nitrobenzoic acid (4.86 g, 24.42 mmol) and SnCl2 (16.5 g, 72.36 mmol) in EtOAc was heated at 70° C. overnight. After cooling at rt, the pH was adjusted to 7-8 with satd. aq. NaHCO3. The mixture was extracted with EtOAc, and the organic layer was washed with brine, filtered through diatomaceous earth, and dried over Na2SO4 to provide the title compound, which was used without further purification. ESI-MS (m/z): 170 [M+1]+.

Workup

  1. temperatureAfter cooling at rt
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. filtrationfiltered through diatomaceous earth
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-fb9a274d3d724005b66f92d11eca9c4f
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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