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Hydrochloric Acid → 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde oxime

HRID 1022835
Notes
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Reaction equation

HRID 1022835 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16]([CH3:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[NH2:28][OH:29].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=[N:28][OH:29])=[C:16]([CH3:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 866585204-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde2×

Product 1

HCID 1363862674-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde oximeYield 91%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde (i.e. the product of Step 1, 5.00 g), hydroxylamine hydrochloride (1.30 g) and concentrated hydrochloric acid (1 mL, 1.05 g) in MeOH (methanol) (37.5 mL) was stirred at 70° C. for 4 h. After cooling, the mixture was freed from all volatiles by evaporation and partitioned between MTBE and water. The organic layer was separated and dried. Chromatography over silica gel yielded the title compound (4.70 g, 91%).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was freed from all volatiles by evaporation
  3. custompartitioned between MTBE and water
  4. customThe organic layer was separated
  5. customdried

Sources & evidence

ORD record
ord-6ffc7733c34b4b08aa4e6990c946f8ae
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722673B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes