Sodium Bicarbonate → 6-bromo-N4-phenylpyridine-3,4-diamine

HRID 1986366Notes

Reaction equation

HRID 1986366 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([N+:15]([O-])=O)=[CH:4][N:3]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH2:15])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 860451242-Bromo-5-nitro-N-phenyl-4-pyridineamine

Product 1

HCID 860451276-bromo-N4-phenylpyridine-3,4-diamineYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

The product from Step 3 (7.42 g, 25.2 mmol) in acetic acid (80 mL) was treated with iron powder (5.65 g, 100.95 mmol) portionwise over 1 h while the temperature was maintained between 70-80° C. The hot reaction mixture was quickly filtered through a pad of celite and washed with methanol. The combined filtrates concentrated to give a dark red residue was treated with NaHCO3 and extracted with ethyl acetate. The organic layers were washed brine, dried over Na2SO4 and concentrated to afford the title compound (6.1 g, 95%). MS (ES+) m/e 264/266 [M+H]+.

Workup

  1. filtrationThe hot reaction mixture was quickly filtered through a pad of celite
  2. washwashed with methanol
  3. concentrationThe combined filtrates concentrated
  4. customto give a dark red residue
  5. extractionextracted with ethyl acetate
  6. washThe organic layers were washed brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-edeb92b462514c8d92159e45c40552d2
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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