Dimethylformamide → 4-Amino-5-ethoxy-2-fluorobenzoic acid

HRID 2234445Notes

Reaction equation

HRID 2234445 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([N+:14]([O-])=O)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])[CH3:2].CN(C=O)C>C(O)C.[Pd]>[NH2:14][C:5]1[C:4]([O:3][CH2:1][CH3:2])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([F:13])[CH:6]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 686832655-Ethoxy-2-fluoro-4-nitrobenzoic acid2×

Product 1

HCID 686826134-Amino-5-ethoxy-2-fluorobenzoic acidYield 40.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-ethoxy-2-fluoro-4-nitrobenzoic acid (Intermediate 172; 1.24 g, 5.40 mmol) was stirred and dissolved in ethanol:DMF (50 mL:5 mL) over 5% Pd/C (125 mg) and hydrogenated at ambient temperature for 4 hours. The catalyst was filtered and washed with ethanol and the solvent evaporated. The resultant material was purified on a silica column, eluting with 0-5% MeOH/DCM. Product containing fractions were combined and evaporated to yield the title compound as a pale brown solid (433 mg, 40%)

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethanol
  3. customthe solvent evaporated
  4. customThe resultant material was purified on a silica column
  5. washeluting with 0-5% MeOH/DCM
  6. additionProduct containing fractions
  7. customevaporated

Sources & evidence

ORD record
ord-43c4891465bf4f35aac60f37de798089
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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