Sodium Carbonate → HCID 178513342, compound

HRID 876623Notes

Reaction equation

HRID 876623 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[F:10])#[N:2].C([O-])([O-])=O.[Na+].[Na+].[NH2:17][OH:18].Cl>CCO.O>[NH2:7][C:6]1[CH:8]=[CH:9][C:3]([C:1](=[NH:2])[NH:17][OH:18])=[C:4]([F:10])[CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 27834134-Amino-2-fluorobenzonitrile

Product 1

HCID 178513342HCID 178513342, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

4-cyano-3-fluoroaniline (10 g, 0.0735 mol) was dissolved in EtOH (36.7 ml) and water (7.3 ml), Na2CO3 (5.06 g, 0.65 eq) was added. The mixture was heated at 60° C. and a solution of NH2OH.HCl (5.615 g, 1.1 eq) in water (7.3 ml) was added slowly, the mixture was heated at 60° C. overnight. The mixture was cooled to 0° C., and the solid collected by filtration. Washed with water (7 ml), EtOH (7 ml), Et2O (20 ml) and dried to give 7.5 g of compound 139-1.

Workup

  1. temperaturethe mixture was heated at 60° C. overnight
  2. temperatureThe mixture was cooled to 0° C.
  3. filtrationthe solid collected by filtration
  4. washWashed with water (7 ml), EtOH (7 ml), Et2O (20 ml)
  5. customdried

Sources & evidence

ORD record
ord-8bac4e852f434bd997f8f283cc1cc470
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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