Hydroxyamine hydrochloride → HCID 86745844, compound

HRID 1196615Notes

Reaction equation

HRID 1196615 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[Cl:7][C:8]1[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]([Cl:24])[C:9]=1[NH:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14]>CO>[Cl:7][C:8]1[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]([Cl:24])[C:9]=1[NH:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13](=[N:2][OH:3])[NH2:14]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 19898990HCID 19898990, compound

Product 1

HCID 86745844HCID 86745844, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a room temperature solution of hydroxylamine hydrochloride (1.362 g, 19.62 mmols) in 40 mL of methanol is added sodium methoxide (1.030 g, 19.06 mmols). The mixture is stirred at room temperature for 15 minutes, then filtered. The filtrate is added to a suspension of 2-(2,6-dichloro-3-methylanilino)benzonitrile (3.109 g, 11.20 mmols) [prepared according to Juby, J. Med. Chem., 11, 111 (1968)] in 70 mL of methanol and the mixture is heated at reflux overnight. The clear yellow solution is cooled and concentrated in vacuo. Flash chromatography eluting with 6:1 hexane: ethyl acetate provides 2.079 g (60%) of 2-(2,6-dichloro-3-methylanilino)benzamide oxime as a white solid.

Workup

  1. filtrationfiltered
  2. temperaturethe mixture is heated
  3. temperatureat reflux overnight
  4. temperatureThe clear yellow solution is cooled
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography eluting with 6:1 hexane

Sources & evidence

ORD record
ord-6a330d5966234420a03e0639c18b2f33
Source dataset
uspto-grants-1992_05
Patent number
US05114958

Reaction notes

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