Hydrochloric Acid → HCID 59740600, compound

HRID 557531Notes

Reaction equation

HRID 557531 reaction equation
[Br:1][C:2]1[C:3](=[O:19])[N:4]([CH3:18])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[C:9]=2[CH3:17])[CH:7]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>[Fe].C(O)C>[NH2:14][C:10]1[C:9]([CH3:17])=[C:8]([C:6]2[CH:7]=[C:2]([Br:1])[C:3](=[O:19])[N:4]([CH3:18])[CH:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 59740601HCID 59740601, compound

Product 1

HCID 59740600HCID 59740600, compoundYield 111.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A 50-mL single-neck round-bottomed flask equipped with a mechanical stirrer was charged with 3-bromo-1-methyl-5-(2-methyl-3-nitrophenyl)pyridin-2-one (11) (0.70 g, 2.17 mmol), ethanol (15 mL), iron powder (−325 mesh, 1.20 g, 21.7 mmol), 2N hydrochloric acid (1.09 mL, 2.17 mmol) and stirred at reflux for 4 h. After this time the reaction was cooled to room temperature and solid potassium carbonate (0.738 g, 5.35 mmol) was added. The suspension was stirred for 0.5 h and then filtered through a pad of Celite 521. The filter cake was washed with ethanol (3×15 mL) and the combined filtrates were concentrated to a constant weight under reduced pressure to afford 0.71 g (88%) of 5-(3-amino-2-methylphenyl)-3-bromo-1-methylpyridin-2-one (12) as a yellow oil: 1H NMR (300 MHz, CDCl3) 7.75 (dd, 1H, J=2.1 Hz), 7.23 (d, 1H, J=2.1 Hz), 7.05 (t, 1H, J=7.8 Hz), 6.72 (d, 1H, J=7.8 Hz), 6.60 (d, 1H, J=7.2 Hz), 3.75 (br s, 2H), 3.66 (s, 3H), 2.07 (s, 3H); MS (ESI+) m/z 293 (M+H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a mechanical stirrer
  2. temperatureat reflux for 4 h
  3. stirringThe suspension was stirred for 0.5 h
  4. filtrationfiltered through a pad of Celite 521
  5. washThe filter cake was washed with ethanol (3×15 mL)
  6. concentrationthe combined filtrates were concentrated to a constant weight under reduced pressure

Sources & evidence

ORD record
ord-6f538291232b4ba8b81c5e5f2fd96991
Source dataset
uspto-grants-2011_11
Patent number
US08058446B2

Reaction notes

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