Ammonium Chloride → 5-Bromopyridine-2,3-diamine

HRID 1910674Notes

Reaction equation

HRID 1910674 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[Cl-].[NH4+]>C(O)(C)C.O.CCOC(C)=O.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 1388782-Amino-5-bromo-3-nitropyridine

Product 1

HCID 6911565-Bromopyridine-2,3-diamineYield 95%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

5-Bromo-3-nitropyridin-2-amine (3 g) was dissolved in isopropyl alcohol (56 mL) and water (28 mL). Ammonium chloride (1.47 g, 2 eq) was added followed by iron powder (2.31 g, 3 eq). The reaction was heated to 90° C. for 45 minutes. The solution was then cooled, and diluted with EtOAc, filtered, and the layers were separated. The organic layer was then washed with brine, dried over sodium sulfate, and concentrated delivering product as a solid (2.45 g, 95% yield). 1H-NMR (300 MHz, DMSO-d6) δ 7.25 (d, 1H), 6.77 (d, 1H), 5.70-5.40 (bs, 2H), 5.20-4.80 (bs, 2H).

Workup

  1. temperatureThe solution was then cooled
  2. filtrationfiltered
  3. customthe layers were separated
  4. washThe organic layer was then washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-38336f08df4b44ce8ee82e90ae2dab56
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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