Hydrochloric Acid → HCID 178433877, compound

HRID 386374Notes

Reaction equation

HRID 386374 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])/[C:12](=[N:15]\[NH:16][C:17]3[C:18]([OH:32])=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29](Cl)=[O:30])[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)/[C:11]([CH3:33])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].N.C[N:36]1C(=O)CCC1.Cl>CCO>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[C:18]([OH:32])=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH2:36])=[O:30])[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[C:11]([CH3:33])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21712033NH3 NmpHCID 178433878HCID 178433878, compound

Product 1

HCID 178433877HCID 178433877, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

(Z)-3′-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)hydrazinyl)-2′-hydroxybiphenyl-3-carbonyl chloride (5 g, 10.9 mmol) was added portion wise (over one hour) to an NH3/NMP solution (120 mL) and the resulting reaction mixture was cooled to 0° C. The cooled reaction mixture was stirred for one hour, then warmed to room temperature and EtOH (50 mL) was added followed by drop wise addition of 4 M HCl (100 mL). The resulting orange suspension was stirred for half an hour, filtered, washed with 2×50 mL EtOH. The filtered orange crystals were suspended in EtOAc (50 mL) and refluxed for 4 hours, then cooled to room temperature and 20 mL of MeOH/H2O (1/1) were added. the resulting orange suspension was filtrated, washed with MeOH/H2O=1/1 (30 mL) and dried in vacuum oven (0 bar/50° C.) for four hours giving 2.54 g of fluorescent orange crystals of Z)-3′-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)hydrazinyl)-2′-hydroxybiphenyl-3-carboxamide (Yield: 50.9%; HPLC purity: 98%).

Workup

  1. customthe resulting reaction mixture
  2. customThe cooled reaction mixture
  3. temperaturewarmed to room temperature
  4. stirringThe resulting orange suspension was stirred for half an hour
  5. filtrationfiltered
  6. washwashed with 2×50 mL EtOH
  7. temperaturerefluxed for 4 hours
  8. temperaturecooled to room temperature
  9. addition20 mL of MeOH/H2O (1/1) were added
  10. filtrationthe resulting orange suspension was filtrated
  11. washwashed with MeOH/H2O=1/1 (30 mL)
  12. customdried in vacuum oven (0 bar/50° C.) for four hours

Sources & evidence

ORD record
ord-3f6999ef36fe4de88e517a2ec0c54897
Source dataset
uspto-grants-2013_02
Patent number
US08372822B2

Reaction notes

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