Sodium Carbonate → HCID 178513326, compound

HRID 1989136Notes

Reaction equation

HRID 1989136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]#[N:15])[CH:11]=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].C(=O)([O-])[O-].[Na+].[Na+]>CCO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([C:14]([NH:21][OH:22])=[NH:15])[CH:11]=[C:10]([C:16]([F:19])([F:17])[F:18])[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 57468704HCID 57468704, compound

Product 1

HCID 178513326HCID 178513326, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(4-chloro-phenyl)-4-trifluoromethyl-pyridine-2-carbonitrile (example B.5) (3.6 g, 13 mmol), hydroxylamine-hydrochloride (3.275 g, 47 mmol) and sodium carbonate (2.7 g, 47 mmol) in EtOH (60 ml) and water (60 ml) was stirred under argon atmosphere at 100° C. for 4 h. The EtOH was evaporated, the mixture was diluted with water and stirred for 1 h at 0° C. The crude product was filtered and dried in HV to give the pure title compound as a light yellow solid (3.54 g, 88%). MS (ISP) 316.1 [(M+H)+] and 318 [(M+2+H)+]; mp 180-186° C.

Workup

  1. customThe EtOH was evaporated
  2. additionthe mixture was diluted with water
  3. stirringstirred for 1 h at 0° C
  4. filtrationThe crude product was filtered
  5. customdried in HV

Sources & evidence

ORD record
ord-c906853ba62948be9bd6057944cc3f89
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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