Sulfuric Acid → HCID 17953125, compound

HRID 1527856Notes

Reaction equation

HRID 1527856 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[N:6][CH:7]=1.[OH:11]S(O)(=O)=O>CCO.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH2:10])=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 150054172-(5-Bromopyridin-3-yl)acetonitrile

Product 1

HCID 17953125HCID 17953125, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

(5-Bromo-pyridin-3-yl)-acetonitrile (1 g, 5.1 mmol) was dissolved in a mixture of EtOH (20 ml) and water (1.2 ml). H2SO4 (6.8 ml) was then added to the mixture and the mixture was heated at ˜110° C. for 24 hrs. Solvent was removed under vacuo, taken up in EtOAc and washed with 2N Na2CO3 solution. Drying and evaporation gave a crude oil which was sufficiently pure for the next step. Alternatively, the above crude was dissolved in 7N NH3— MeOH (20 ml) and stirred at R.T over the weekend. Solvent was evaporated and purified by flash column eluting with DCM-MeOH (95:5) to obtain a yellow colored material (0.9 g).

Workup

  1. customSolvent was removed under vacuo
  2. washwashed with 2N Na2CO3 solution
  3. customDrying
  4. customevaporation
  5. customgave a crude oil which
  6. customSolvent was evaporated
  7. custompurified by flash column
  8. washeluting with DCM-MeOH (95:5)

Sources & evidence

ORD record
ord-e3d5dc4638df4b7094611e55d22fbe92
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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