Benzyl 2-(2-fluoro-4-nitrobenzamido)acetate → 2-(4-Amino-2-fluorobenzamido)acetic acid

HRID 1399441Notes

Reaction equation

HRID 1399441 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5]>CCOC(C)=O.[Pd]>[NH2:22][C:20]1[CH:19]=[CH:18][C:3]([C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5])=[C:2]([F:1])[CH:21]=1

Participants

4

Reactant 1

HCID 86713116Benzyl 2-(2-fluoro-4-nitrobenzamido)acetate

Product 1

HCID 235078632-(4-Amino-2-fluorobenzamido)acetic acidYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 2-(2-fluoro-4-nitrobenzamido)acetate (100 mg) in EtOAc (10 mL) was added Pd/C (10%, 100 mg) at rt and stirred under the atmosphere of H2 gas for 30 min. The reaction mixture was filtered and washed with EtOAc (2×5 mL). The residue obtained after evaporation of the solvents was recrystallized from EtOAc to give the product as a white color solid (50 mg, 79%), mp 194-196° C. 1H NMR (400 MHz, DMSO-d6): δ 12.53 (1H, br s), 7.74-7.78 1H, m), 7.52 (1H, t, J=8.8 Hz), 6.42 (1H, dd, J=8.4, 1.6 Hz), 6.31 (1H, d, J=14.4 Hz), 5.99 (2H, s), 3.90 (2H, d, J=5.6 Hz); 13C NMR (100 MHz, DMSO-d6): δ 171.3, 163.4 (d, J=3.0 Hz), 161.7 (d, J=244 Hz), 153.8 (d, J=13.0 Hz), 131.9 (d, J=5.0 Hz), 109.6, 107.8 (d, J=12.0 Hz), 99.1 (d, J=26.0 Hz), 41.3; LC-MS (negative ion mode): m/z 211 (M−H)−.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with EtOAc (2×5 mL)
  3. customThe residue obtained
  4. customafter evaporation of the solvents
  5. customwas recrystallized from EtOAc

Sources & evidence

ORD record
ord-44e29f326832489da421d10bdf7170db
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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