Benzyl 2-(2-fluoro-5-nitrobenzamido)acetate → 2-(5-Amino-2-fluorobenzamido)acetic acid

HRID 1399449Notes

Reaction equation

HRID 1399449 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5]>CO.[Pd]>[NH2:22][C:19]1[CH:20]=[CH:21][C:2]([F:1])=[C:3]([CH:18]=1)[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5]

Participants

4

Reactant 1

HCID 86713120Benzyl 2-(2-fluoro-5-nitrobenzamido)acetate

Product 1

HCID 867131212-(5-Amino-2-fluorobenzamido)acetic acidYield 65.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of benzyl 2-(2-fluoro-5-nitrobenzamido)acetate (120 mg) in methanol (10 mL) was added Pd/C (100 mg) at rt and stirred under the atmosphere of H2 gas at rt for 30 min. Work-up of the reaction mixture as described in example 1 gave the product as a pale brown color solid (50 mg, 65%), mp 252-254° C. 1H NMR (400 MHz, DMSO-d6): δ 7.71-7.73 (1H, m), 7.00-7.02 (1H, m), 6.94 (1H, t, J=10.0 Hz), 6.65-6.67 (1H, m), 5.15 (2H, br s), 3.64 (2H, br s); LC-MS (negative ion mode): m/z 211 (M−H)−.

Sources & evidence

ORD record
ord-e17547f298ae476688d824bb09022c90
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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