Hydrochloric Acid → HCID 86668975, compound

HRID 1410134Notes

Reaction equation

HRID 1410134 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[N:10]=[C:9]([CH2:20][CH2:21][CH3:22])[C:8]=2[CH:23]=O)=[C:5]([CH3:25])[O:4][N:3]=1.Cl.[NH2:27][OH:28].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]([O:18][CH3:19])=[CH:16][CH:17]=3)[N:10]=[C:9]([CH2:20][CH2:21][CH3:22])[C:8]=2[CH:23]=[N:27][OH:28])=[C:5]([CH3:25])[O:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86668974HCID 86668974, compound

Product 1

HCID 86668975HCID 86668975, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

The semi-crude 5-(3,5-dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-3-propyl-1H-pyrazole-4-carbaldehyde from step (d) was mixed with hydroxylamine hydrochloride (200 mg, 2.89 mmol) and pyridine (0.3 mL, 3.71 mmol) in dry ethanol (3 mL) and heated at 150° C. for 10 minutes in the microwave. 1 M HCl and CH2Cl2 were added and the phases were separated. The oxime was purified on preparative IIPLC, to give 5-(3,5-dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-3-propyl-1H-pyrazole-4-carbaldehyde oxime (13 mg, 0.037 mmol).

Workup

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

Sources & evidence

ORD record
ord-02059d07b49c4e1d9ff6dd28e3cc1d2f
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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