Pyridine → HCID 19363503, compound

HRID 850415Notes

Reaction equation

HRID 850415 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=[O:12].CI.CC(C)([O-])C.[K+].Cl.[NH2:28][NH:29][C:30]([NH2:32])=[O:31].N1C=CC=CC=1>CO.CCOCC.C1C=CC=CC=1>[NH2:28][NH:29][C:30]([NH2:32])=[O:31].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=[O:12]

Participants

9

Reactant 5

HCID 1049PyridineHCID 6328Methyl iodideHCID 11236Semicarbazide hydrochlorideHCID 19363318HCID 19363318, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19363503HCID 19363503, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-5 °C

Procedure

2-(2-Methoxy-5-methylphenyl)octanal (63.8 g, 0.257 mol), methyl iodide (160 ml, 2.57 mol) and benzene (300 ml) were mixed, and this solution was cooled to -5° C. Potassium t-butoxide (31.3 g, 0.279 mol) was added in such a manner that the temperature of the reaction mixture does not exceed 0° C., and the mixture was stirred at -2° C. for 0.5 hour. The reaction mixture was poured into ice water (200 ml) to stop the reaction. The aqueous layer was erected twice with ether (150 ml), and the organic layers were combined, washed with saturated brine (100 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. Methanol (400 ml), an aqueous solution (110 ml) of semicarbazide hydrochloride (28.6 g, 0.257 mol) and pyridine (20.4 ml, 0.257 mol) were added to the obtained residue, and the mixture was stirred at room temperature for 0.75 hour. The precipitated crystals were collected by filtration, and washed with hexane. The crystals were dried to give 2-(2-methoxy-5-methylphenyl)octanal semicarbazide (64.7 g, 79%) as colorless crystals.

Workup

  1. customdoes not exceed 0° C.
  2. customthe reaction
  3. washwashed with saturated brine (100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. stirringthe mixture was stirred at room temperature for 0.75 hour
  8. filtrationThe precipitated crystals were collected by filtration
  9. washwashed with hexane
  10. customThe crystals were dried

Sources & evidence

ORD record
ord-a41ed2f97781426dab26fc76113ded29
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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