Water → 2-Acetamido-6-bromo-3-nitropyridine

HRID 2181018Notes

Reaction equation

HRID 2181018 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Br:11])[N:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].S(=O)(=O)(O)O.O>C(O)(=O)C.CCOCC>[C:12]([NH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Br:11])[N:3]=1)(=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 120977456-Bromo-3-nitro-2-pyridinamine

Product 1

HCID 223878242-Acetamido-6-bromo-3-nitropyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 2-amino-6-bromo-3-nitropyridine (23.9 g) in acetic acid (48 ml) were added acetic anhydride (48 ml) and sulfuric acid (2.9 ml), and the mixture was heated at 65° C. for 40 min. The reaction mixture once became homogeneous and a product soon precipitated to give a suspension. The reaction mixture was allowed to cool and poured into cold water (480 ml), which was followed by stirring for 30 min. The precipitate was collected by filtration and washed with water to give a crude product. This was suspended in ether (60 ml) and collected by filtration to give 2-(acetamido)-6-bromo-3-nitropyridine as a pale-yellow powder (27.2 g).

Workup

  1. customThe reaction mixture once became homogeneous and a product soon precipitated
  2. customto give a suspension
  3. temperatureto cool
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customto give a crude product
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-df338178af24406e893e6e18e04f74e2
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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