Ammonia → 2-Bromo-5-nitropyridin-4-amine

HRID 1986383Notes

Reaction equation

HRID 1986383 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](Br)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.N.C([N:15](CC)CC)C>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([NH2:15])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8471TriethylamineHCID 160998502,4-Dibromo-5-nitropyridine

Product 1

HCID 130404032-Bromo-5-nitropyridin-4-amineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, to a solution of 2,4-dibromo-5-nitropyridine in THF (150 mL), was added ammonia (2.0M in MeOH), followed with triethylamine (5 mL). This mixture was then stirred at rt for 50 h. The reaction mixture was concentrated, taken up in EtOAC, filtered through a silica gel pad, and then concentrated in vacuo to afford the title compound (3.67 g, 95%). MS (ES+) m/e 218 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered through a silica gel pad
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f043e6856ecf4bfa9286253395450d1c
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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