Trifluoroacetic acid → methyl 2-amino-6-chloro-3-nitrobenzoate

HRID 2253310Notes

Reaction equation

HRID 2253310 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([NH:12]CC2C=CC(OC)=CC=2)[C:5]([N+:22]([O-:24])=[O:23])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>CCOC(C)=O.O>[NH2:12][C:6]1[C:5]([N+:22]([O-:24])=[O:23])=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium Bicarbonate2×HCID 59645475HCID 59645475, compound

Product 1

HCID 59645472methyl 2-amino-6-chloro-3-nitrobenzoateYield 81.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of methyl 6-chloro-2-[(4-methoxybenzyl)amino]-3-nitrobenzoate (13.2 g, 37.6 mmol) and TFA (75 mL) was stirred at room temperature for 1.7 h. The mixture was diluted with EtOAc (500 mL) and water (250 mL). Solid NaHCO3 (125 g) was slowly added to the heterogeneous mixture. Saturated aqueous NaHCO3 solution (200 mL) and EtOAc were added and the phases were separated. The organic layer was washed with saturated aqueous NaHCO3 solution (150 mL) and brine (50 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (10-40μ silica gel; hexane:EtOAc 5:1) to yield the title compound (7.03 g, 81% yield) as a yellow solid.

Workup

  1. customthe phases were separated
  2. washThe organic layer was washed with saturated aqueous NaHCO3 solution (150 mL) and brine (50 mL)
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (10-40μ silica gel; hexane:EtOAc 5:1)

Sources & evidence

ORD record
ord-5be70adccc3445d89018d575ef4757ea
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

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