Hydrochloric Acid → HCID 136227081, compound

HRID 1391333Notes

Reaction equation

HRID 1391333 reaction equation
[OH:1][C:2]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=O.[OH-:18].[K+].Cl.[NH2:21]O.Cl>C(O)C.O>[OH:1][C:2]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4](=[N:21][OH:18])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 223484(4-Chlorophenyl)(2-hydroxy-3-methylphenyl)methanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 136227081HCID 136227081, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The ketone of Example 4 (7.5 g, 0.03 mole) in ethanol (18 ml.) was added with stirring to a solution of (85%) potassium hydroxide (20.74 g, 0.3 mole) in water (85 ml) at 10° C., this colloidal solution was treated with solid hydroxylamine hydrochloride (8.54 g, 0.12 mole) and stirred overnight. The solution was acidified with 5N HCl to give a solid, which was filtered, washed with water and stirred for 45 minutes, then treated with 5% Na2CO3 solution (30.5 ml), to remove unwanted oxime stereoisomer, filtered, washed with 5% Na2CO3 solution (100 ml) and then with water until free of alkali. The dried solid had m.p. 175°-177° C. Recrystallisation from 54% benzene-light petroleum (b.p. 60°-80° C.) mixture gave the oxime, m.p. 178° C. ("bonded isomer") 5.45 g.

Workup

  1. customto give a solid, which
  2. filtrationwas filtered
  3. washwashed with water
  4. stirringstirred for 45 minutes
  5. additiontreated with 5% Na2CO3 solution (30.5 ml)
  6. customto remove unwanted oxime stereoisomer
  7. filtrationfiltered
  8. washwashed with 5% Na2CO3 solution (100 ml)
  9. customRecrystallisation from 54% benzene-light petroleum (b.p. 60°-80° C.) mixture

Sources & evidence

ORD record
ord-e1375a59908a41979d5707030ec675bb
Source dataset
uspto-grants-1979_02
Patent number
US04141995

Reaction notes

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