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

HRID 1399446Notes

Reaction equation

HRID 1399446 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][CH2:9][C:10]([O:12]CC2C=CC=CC=2)=[O:11])=[O:7])=[CH:4][C:3]=1[N+:22]([O-])=O>CCOC(C)=O.[Pd]>[NH2:22][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:2]=1[F:1])[C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7]

Participants

4

Reactant 1

HCID 86713118Benzyl 2-(4-fluoro-3-nitrobenzamido)acetate

Product 1

HCID 734378302-(3-Amino-4-fluorobenzamido)acetic acidYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 2-(4-fluoro-3-nitrobenzamido)acetate (85 mg) in EtOAc (10 mL) was added Pd/C (10%, 100 mg) at rt and stirred under the atmosphere of H2 gas for 25 min. Work-up of the reaction mixture as described in example 1 gave the product as a white color solid (38 mg, 70%), mp 150-152° C. 1H NMR (400 MHz, CDCl3+DMSO-d6): δ 7.74 (1H, br s), 7.37 (1H, dd, J=8.6, 1.8 Hz), 7.12-7.16 (1H, m), 6.97 (1H, dd, J=10.6, 8.6 Hz), 4.07 (2H, d, J=5.6 Hz); 13C NMR (100 MHz, CDCl3+DMSO-d6): δ 170.6, 165.9, 151. 9 (d, J=242 Hz), 134.5 (d, J=13 Hz), 129.6 (d, J=3 Hz), 115.4 (d, J=8 Hz), 115.1 (d, J=6 Hz), 113.6 (d, J=19 Hz), 40.5; LC-MS (negative ion mode): m/z 211 (M−H)−.

Sources & evidence

ORD record
ord-0c95adb23b0343bda67f1ae9c4c371b0
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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