Ethyl Acetate → 2-Amino-4-bromopyridine-3-carbonitrile

HRID 2361743Notes

Reaction equation

HRID 2361743 reaction equation
Br[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[C:4]#[N:5].CCOC(C)=O.[NH4+:17].[OH-]>C1COCC1>[NH2:17][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 574595912,4-Dibromopyridine-3-carbonitrile

Product 1

HCID 580811212-Amino-4-bromopyridine-3-carbonitrileYield 26.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of compound D7 (32 g, 122.2 mmol) in NH4OH (200 ml, 30% in water) and THF (200 ml) was heated at 100° C. for 12 h. in a PARR pressure vessel. After cooling, EtOAc was added. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The solid residue thus obtained was triturated with DCM and then filtered off. The filtrate was evaporated in vacuo to yield compound D8 (6.5 g, 26.8%) as a white solid.

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe solid residue thus obtained
  7. customwas triturated with DCM
  8. filtrationfiltered off
  9. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-b0c1fb4648cf453d845e32f0ef0125d0
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

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