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

HRID 1699933Notes

Reaction equation

HRID 1699933 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 mixture was uniform so that it quickly became a suspension containing a precipitate. After cooling, the reaction mixture was poured into cold water (480 ml) and the mixture was stirred for 30 min. The precipitate was collected by filtration and washed with water to give a crude product. The crude product was suspended in ether (60 ml) and collected by filtration to give the objective compound (27.2 g) as a pale-yellow powder.

Workup

  1. additioncontaining a precipitate
  2. temperatureAfter cooling
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customto give a crude product
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-8d9605a9f672454f94ff5046396b38e6
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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