Hydrochloric Acid → HCID 75606758, compound

HRID 242179Notes

Reaction equation

HRID 242179 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[N:10]=[C:9]([CH3:19])[C:8]=2[CH:20]=O)=[C:5]([CH3:22])[O:4][N:3]=1.Cl.[NH2:24][OH:25].N1C=CC=CC=1.Cl>C(O)C.C(Cl)Cl>[CH3:1][C:2]1[C:6]([C:7]2[N:11]([C:12]3[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=3)[N:10]=[C:9]([CH3:19])[C:8]=2[CH:20]=[N:24][OH:25])=[C:5]([CH3:22])[O:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86668973HCID 86668973, compound

Product 1

HCID 75606758HCID 75606758, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

The semi-crude 5-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde was mixed with hydroxylamine hydrochloride (100 mg, 0.014 mmol) and pyridine (0.15 mL) in dry ethanol (1.5 mL) and heated at 150° C. for 10 min in the microwave. 1 M HCl and CH2Cl2 were added and the phases were separated. The oxime was purified on preparative HPLC to give E3 5-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbaldehyde oxime (37 mg, 50%). Identification of the title compound by 1H-NMR showed that the product was an approximately 1:1 mixture of the (E) and (Z) oxime isomers. ES/MS m/z: 313.17 (M+H), 311.19 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.83 s 1H, 7.13 m 2H, 6.87 m 2H; 2.41 s 3H, 1.88 s 3H.

Workup

  1. customthe phases were separated
  2. customThe oxime was purified on preparative HPLC

Sources & evidence

ORD record
ord-93f44dfcc7df4869b73a953364e1a2bc
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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