Nitric Acid → 6-Bromo-5-nitropyridin-2-amine

HRID 869879Notes

Reaction equation

HRID 869879 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C)[CH:5]=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10353221N-(6-bromopyridin-2-yl)acetamide

Product 1

HCID 130404066-Bromo-5-nitropyridin-2-amineYield 86%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of N-(6-bromopyridin-2-yl)acetamide (9.0 g, 40 mmol) in H2SO4 (100 mL) was added HNO3 (69%, 5.5 g, 60 mmol) dropwise at 0° C. The mixture was stirred at this temperature for 4 hours, and was then poured into ice-water. The mixture was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give 6-bromo-5-nitropyridin-2-amine (7.5 g, 82%). 1H NMR (400 MHz, DMSO) δ 8.10 (d, J=8.8 Hz, 1H), 7.73 (brs, 2H), 6.46 (d, J=8.8 Hz, 1H).

Workup

  1. extractionThe mixture was extracted with EtOAc (100 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-96dd29682c3c46e58660741bc9a65712
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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