Hydrochloric Acid → HCID 68607260, compound

HRID 2203203Notes

Reaction equation

HRID 2203203 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=1[CH3:12].Cl.CCO>[Fe].C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([CH3:11])=[CH:6][C:7]=1[NH2:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6610498HCID 6610498, compound

Product 1

HCID 68607260HCID 68607260, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-1,5-dimethyl-3-nitrobenzene (1.8 g, 7.8 mmol), Fe powder (2.2 g), concentrated hydrochloric acid (0.3 mL), and EtOH (20 mL) was stirred at 80° C. overnight. Ethyl acetate (20 mL) was subsequently added. The resulting suspension was filtered and the filtrate concentrated. The residue was treated with H2O (10 mL), extracted with ethyl acetate (2×20 mL), washed with brine, dried over anhydrous Na2SO4, and concentrated to give the title compound as a solid (1.2 g, 77%).

Workup

  1. filtrationThe resulting suspension was filtered
  2. concentrationthe filtrate concentrated
  3. additionThe residue was treated with H2O (10 mL)
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9c0f5387b437420a95ba1b29f142c12a
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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