Benzyl 2-(3-fluoro-4-nitrobenzamido)acetate → 2-(4-Amino-3-fluorobenzamido)acetic acid

HRID 1399451Notes

Reaction equation

HRID 1399451 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O)[C:5]([NH:7][CH2:8][C:9]([O:11]CC1C=CC=CC=1)=[O:10])=[O:6]>CCOC(C)=O.[Pd]>[NH2:22][C:21]1[CH:20]=[CH:19][C:4]([C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 86713122Benzyl 2-(3-fluoro-4-nitrobenzamido)acetate

Product 1

HCID 159257412-(4-Amino-3-fluorobenzamido)acetic acidYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 2-(3-fluoro-4-nitrobenzamido)acetate (200 mg) in EtOAc (10 mL) was added Pd/C (10%, 200 mg) at rt and stirred under the atmosphere of H2 gas for 20 min. Work-up of the reaction mixture as described in example 1 gave product as an off-brown color solid (100 mg, 79%), mp 198-200° C. 1H NMR (400 MHz, DMSO-d6): δ 12.52 (1H, br s), 8.45 (1H, br s), 7.52 (1H, d, J=13.2 Hz), 7.47 (1H, d, J=8.0 Hz), 6.77 (1H, t, J=8.4 Hz), 5.71 (2H, s), 3.87 (2H, d, J=5.2 Hz); 13C NMR (100 MHz, DMSO-d6): δ 171.5, 165.5, 149.5 (d, J=235 Hz), 139.7 (d, J=13.0 Hz), 124.3 (d, J=2.0 Hz), 121.1 (d, J=6.0 Hz), 114.8 (d, J=4.0 Hz), 114.0 (d, J=20.0 Hz), 41.2; LC-MS (negative ion mode): m/z 211 (M−H)−.

Sources & evidence

ORD record
ord-21df880766df40209ac62c0cdd7e4162
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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