Acetic acid 6-fluoro-3-nitro-2-phenylaminobenzyl ester → Acetic acid 3-amino-6-fluoro-2-phenylaminobenzyl ester

HRID 243251Notes

Reaction equation

HRID 243251 reaction equation
[F:1][C:2]1[C:7]([CH2:8][O:9][C:10](=[O:12])[CH3:11])=[C:6]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]([N+:20]([O-])=O)=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[NH2:20][C:5]1[C:6]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([C:2]([F:1])=[CH:3][CH:4]=1)[CH2:8][O:9][C:10](=[O:12])[CH3:11]

Participants

4

Reactant 1

HCID 68156961Acetic acid 6-fluoro-3-nitro-2-phenylaminobenzyl ester

Product 1

HCID 68158130Acetic acid 3-amino-6-fluoro-2-phenylaminobenzyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of acetic acid 6-fluoro-3-nitro-2-phenylaminobenzyl ester (3.2 g, 10.5 mmol) in EtOAc (50 mL) was added palladium on carbon (600 mg, 10% by wt) and the reaction mixture stirred at RT under an atmosphere of hydrogen for 16 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% DCM in cyclohexane) to give the title compound as a brown solid (2.3 mg, 80%). 1H NMR 400 MHz δ (CDCl3): 7.22-7.15 (2H, m), 6.86 (1H, t, J=8.9 Hz), 6.81 (1H, tt, J=7.4, 1.0 Hz), 6.78-6.71 (1H, m), 6.63-6.58 (2H, m), 6.43 (1H, br s), 5.10 (2H, d, J=1.9 Hz), 3.72 (2H, br s), 1.99 (3H, s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. washThe resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% DCM in cyclohexane)

Sources & evidence

ORD record
ord-4e16abe707994dd98571cd2c4bf723e5
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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