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

HRID 1399466Notes

Reaction equation

HRID 1399466 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 86713134(R)-2-(2-Fluoro-6-nitrobenzamido)propanoic acid

Product 1

HCID 86713135(R)-2-(2-Amino-6-fluorobenzamido)propanoic acidYield 72%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of iron powder (1.3 g, 23.42 mmol) in AcOH (12 mL) was added (R)-2-(2-fluoro-6-nitrobenzamido)-propanoic acid (600 mg, 2.34 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 (380 mg, 72%), mp 220-224° C. 1H NMR (400 MHz, DMSO-d6): δ 12.67 (1H, br s), 8.46 (1H, d, J=5.2 Hz), 7.08 (1H, dd, J=14.8, 7.2 Hz), 6.50 (1H, d, J=8.0 Hz), 6.31 (1H, t, J=9.2 Hz), 5.89 (2H, br s), 4.37 (1H, pentet, J=7.2 Hz), 1.35 (3H, d, J=7.2 Hz); LC-MS (positive ion mode): m/z 227 (M+H)+.

Sources & evidence

ORD record
ord-a80344c9d7ca419891a91d2bf2444459
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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