Methyl 5-fluoro-3-methyl-2-nitrobenzoate → Methyl 2-amino-5-fluoro-3-methylbenzoate

HRID 655936Notes

Reaction equation

HRID 655936 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([N+:12]([O-])=O)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>CO.[Pd]>[NH2:12][C:5]1[C:4]([CH3:15])=[CH:3][C:2]([F:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 53415166Methyl 5-fluoro-3-methyl-2-nitrobenzoate

Product 1

HCID 53415135Methyl 2-amino-5-fluoro-3-methylbenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (E2) (1.0 eq.) and Pd/C (10% w/w) in MeOH (0.25 M) was stirred for 3 d at RT under H2 atmosphere (1 atm). The mixture was filtered through Celite® and then the solvent was evaporated under reduced pressure. The white solid was used without further purification in the subsequent step. 1H NMR (400 MHz, DMSO, 300K) δ 7.29 (1H, dd, J=9.5 Hz, J=3.0 Hz), 7.12 (1H, dd, J=9.5 Hz, J=3.0 Hz), 6.36 (2H, br. s), 3.78 (3H, s), 2.11 (3H, s).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customthe solvent was evaporated under reduced pressure
  3. customThe white solid was used without further purification in the subsequent step

Sources & evidence

ORD record
ord-882c7cdf746c4bd586f36b33ab143c12
Source dataset
uspto-grants-2011_12
Patent number
US08071623B2

Reaction notes

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