Hydrochloric Acid → HCID 89825339, compound

HRID 2203210Notes

Reaction equation

HRID 2203210 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([F:11])=[CH:4][C:3]=1[CH3:12].Cl>CCO.[Fe]>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[CH:6][C:7]=1[NH2:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89825521HCID 89825521, compound

Product 1

HCID 89825339HCID 89825339, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-bromo-5-fluoro-1-methyl-3-nitrobenzene (2.0 g, 8.6 mmol), iron powder (2.4 g) in EtOH (20 mL), and concentrated hydrochloric acid (0.3 mL) was refluxed for 5 hours and then filtered and concentrated. Water (10 mL) was added to the residue and the resulting mixture was extracted with ethyl acetate (2×20 mL). The organic phase was washed with brine and concentrated to give the title compound as a solid (1.4 g, 80%). 1H NMR (400 MHz, CDCl3) δ ppm 6.32-6.26 (2H, m), 4.15 (2H, s), 2.27 (3H, s).

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionWater (10 mL) was added to the residue
  5. extractionthe resulting mixture was extracted with ethyl acetate (2×20 mL)
  6. washThe organic phase was washed with brine
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2321c6b9a6074c5f9a7e117b6ddda910
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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