N-bromobutanimide → HCID 56923659, compound

HRID 243580Notes

Reaction equation

HRID 243580 reaction equation
[N+:1]([C:4]1[N:9]=[C:8]([NH2:10])[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:11]N1C(=O)CCC1=O>CC#N>[Br:11][C:5]1[CH:6]=[CH:7][C:8]([NH2:10])=[N:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 27628816-nitropyridin-2-amine

Product 1

HCID 56923659HCID 56923659, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 6-nitro-pyridin-2-ylamine (9) (5.1 g, 18.4 mmol) in MeCN (125 mL) under nitrogen atmosphere, N-bromosuccinimide (3.43 g, 19.3 mmol) was added at 0° C. After 1 hour, another portion of N-bromosuccinimide (3.57 g, 20.1 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirring was continued overnight. The product was precipitated by addition of water (125 mL). The slurry was cooled to 0° C. and precipitated product was isolated by filtration, washed with premixed MeCN:water (1:1) and dried under vacuum at 40° C. to afford 3.8 g of 5-bromo-6-nitro-pyridin-2-ylamine (2).

Workup

  1. waitwas continued overnight
  2. customThe product was precipitated by addition of water (125 mL)
  3. temperatureThe slurry was cooled to 0° C.
  4. customprecipitated product
  5. customwas isolated by filtration
  6. washwashed with premixed MeCN:water (1:1)
  7. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-9aed1c718b7c4f198e925945e1c2f7bb
Source dataset
uspto-grants-2014_02
Patent number
US08653274B2

Reaction notes

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