N-bromobutanimide → 5-Bromo-6-methoxy-3-nitropyridin-2-amine

HRID 1848126Notes

Reaction equation

HRID 1848126 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1.C1C(=O)N([Br:20])C(=O)C1>CN(C=O)C>[Br:20][C:4]1[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[C:7]([NH2:9])=[N:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 38524282-Amino-6-methoxy-3-nitropyridine

Product 1

HCID 534081225-Bromo-6-methoxy-3-nitropyridin-2-amineYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-methoxy-3-nitropyridin-2-amine (1.56 g, 9.2 mmol) in 15 mL of DMF at rt was added N-bromosuccimide (1.81 g, 10.1 mmol) in portions. The resulting mixture was stirred at rt for 1 h. TLC showed the reaction was complete. The reaction mixture was quenched with water and the reddish brown solid was collected by filtration, washed with water, and dried in a vacuum oven to give 5-bromo-6-methoxy-3-nitropyridin-2-amine (2.1 g, 92%). LCMS (ESI) m/z 248, 250 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with water
  2. filtrationthe reddish brown solid was collected by filtration
  3. washwashed with water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-2255b6209dc2441aac3c1b989ef312b5
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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