2-Fluoro-N-methyl-4-nitrobenzamide → 4-Amino-2-fluoro-N-methylbenzamide

HRID 1927378Notes

Reaction equation

HRID 1927378 reaction equation
[CH3:1][NH:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[F:13]>C(OCC)(=O)C.C(O)(=O)C.[Fe]>[CH3:1][NH:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[F:13]

Participants

5

Reactant 1

HCID 534406322-Fluoro-N-methyl-4-nitrobenzamide2×

Product 1

HCID 441395214-Amino-2-fluoro-N-methylbenzamideYield 92%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-Methyl-2-fluoro-4-nitrobenzamide (Formula 38) (0.18 g, 0.91 mmol) and iron (0.31 g, 5.60 mmol) in ethyl acetate (5 mL) and acetic acid (5 mL) was refluxed for 1 h. The solid particles were filtered off. The filtrate was washed with water and extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated and the residue was purified with SiO2 column chromatography (dichloromethane:acetone, 95:5) to give N-Methyl-2-fluoro-4-aminobenzamide (Formula 39) (0.14 g, 92%) as an off-white solid. 1H NMR (acetone-d6) δ 2.86 (d, 3H, J=4.3), 5.50 (br s, 2H), 6.37 (dd, 1H, J=14.7 and 2.1), 6.50 (dd, 1H, J=8.6 and 2.1), 7.06 (br s, 1H), 7.68 (dd, 1H, J=8.8 and 8.8).

Workup

  1. temperaturewas refluxed for 1 h
  2. filtrationThe solid particles were filtered off
  3. washThe filtrate was washed with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customthe residue was purified with SiO2 column chromatography (dichloromethane:acetone, 95:5)

Sources & evidence

ORD record
ord-055de3b9f0234cd2ae2d803b08b054b2
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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