(S)-2-(2-Fluoro-6-nitrobenzamido)propanoic acid → (S)-2-(2-Amino-6-fluorobenzamido)propanoic acid

HRID 1399464Notes

Reaction equation

HRID 1399464 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[C:3]=1[C:4]([NH:6][C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])=[O:5]>CC(O)=O.[Fe]>[NH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])=[O:5]

Participants

4

Reactant 1

HCID 86713132(S)-2-(2-Fluoro-6-nitrobenzamido)propanoic acid

Product 1

HCID 86713133(S)-2-(2-Amino-6-fluorobenzamido)propanoic acidYield 75%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of iron powder (437 mg, 7.81 mmol) in AcOH (5 mL) was added (S)-2-(2-fluoro-6-nitrobenzamido)propanoic acid (200 mg, 0.78 mmol) at rt and stirred at 60-70° C. for 30 min. Work-up of the reaction mixture as described in example 6 gave the product as an off-white color solid (132 mg, 75%), mp 194-198° C. 1H NMR (400 MHz, DMSO-d6): δ 7.97 (1H, br s), 7.05 (1H, dd, J=15.2, 8.0 Hz), 6.49 (1H, d, J=8.4 Hz), 6.37 (2H, br s), 6.28 (1H, dd, J=11.2, 8.4 Hz), 4.14 (1H, br s), 1.30 (3H, d, J=7.2 Hz); 13C NMR (100 MHz, DMSO-d6): δ 176.6, 163.7, 160.7 (d, J=241 Hz), 150.2 (d, J=6 Hz), 131.0 (d, J=12 Hz), 111.5, 106.6 (d, J=19 Hz), 101.2 (d, J=23 Hz), 49.4, 18.1; LC-MS (positive ion mode): m/z 227 (M+H)+.

Sources & evidence

ORD record
ord-f3255a687b384c9997e39aca6738f8ff
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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