Bromine → 2-Amino-5-bromopyridine-3-carbonitrile

HRID 1362251Notes

Reaction equation

HRID 1362251 reaction equation
[Br:1]Br.[NH2:3][C:4]1[N:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7]>CC(O)=O.CCOCC>[NH2:3][C:4]1[N:11]=[CH:10][C:9]([Br:1])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 24408BromineHCID 8182592-Amino-3-cyanopyridine

Product 1

HCID 242291992-Amino-5-bromopyridine-3-carbonitrileYield 78%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Bromine (1.1 mL, 21 mmol) in AcOH (3 mL) was added dropwise to a solution of 2-amino-nicotinonitrile (1.00 g, 8.4 mmol) in AcOH (20 mL) at 10° C. The orange mixture was stirred for 22 hours at ambient temperature then diluted with ether (100 mL). The resultant precipitated salt was filtered, washed with ether and dried on air. The precipitate was suspended in water (100 mL), neutralized with 1N NaOH, filtered, washed with water and dried on air to give 1.29 g (78%) title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.27 (d, J=2.5 Hz, 1H), 8.14 (d, J=2.5 Hz, 1H), 7.13 (s, br, 2H). MS (ESI) m/e: 197.9655 (M+H)+.

Workup

  1. customThe resultant precipitated salt
  2. filtrationwas filtered
  3. washwashed with ether
  4. customdried on air
  5. filtrationfiltered
  6. washwashed with water
  7. customdried on air

Sources & evidence

ORD record
ord-3fb4b88d44ef4174afe710af9ed8e43b
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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