Water → HCID 86146364, compound

HRID 978781Notes

Reaction equation

HRID 978781 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=O.Cl.[NH2:21][OH:22].O>CN(C)C=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[N:21][OH:22]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 13393783HCID 13393783, compound

Product 1

HCID 86146364HCID 86146364, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 27 g 4-chloro-3-formyl-flav-3-ene in 25 ml dimethylformamide is refluxed. To this solution one adds 7.7 g hydroxylamine hydrochloride dissolved in 60 ml dimethylformamide. After two hours reflux, the solution is cooled at room temperature before the addition of 400 ml water. The precipitate is formed, filtered, washed with water and dried. The solid is crystallized in diisopropylether. Pure 4-chloro-3-hydroxyiminomethyl-flav-3-ene is obtained as pale yellow crystals; m.p. 199°-200° C.

Workup

  1. temperatureAfter two hours reflux
  2. customThe precipitate is formed
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. customThe solid is crystallized in diisopropylether

Sources & evidence

ORD record
ord-71746daec5b140ce94d4f92e5ff87e4d
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

Loading…