HCID 23103622, compound → HCID 23103618, compound

HRID 2116507Notes

Reaction equation

HRID 2116507 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:12]=[C:13](Cl)[N:14]=[N:15][C:16]=2[O:17][CH3:18])[OH:10])=[CH:5][CH:4]=1)[CH3:2].C(C1C=CC(C(C2[CH:35]=[C:34]([O:36]C)N=NC=2Cl)O)=CC=1)C>[Pd].C(O)(=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:11]2[CH:12]=[CH:13][N:14]=[N:15][C:16]=2[O:17][CH3:18])=[CH:5][CH:4]=1)[CH3:2].[C:34]([OH:36])(=[O:10])[CH3:35].[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:11]2[CH:12]=[CH:13][N:14]=[N:15][C:16]=2[O:17][CH3:18])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 2

HCID 23103622HCID 23103622, compoundHCID 23103633HCID 23103633, compound

Product 2

HCID 23103618HCID 23103618, compoundHCID 69220153HCID 69220153, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The 6:1 mixture of (4-ethylphenyl)-(3-chloro-6-methoxypyridazin-5-yl)-methanol and (4-ethylphenyl)-(3-chloro-6-methoxypyridazin-4-yl)-methanol (10.7 g), 5% palladium/carbon (5.4 g) and acetic acid (80 ml) were suspended and stirred under a hydrogen atmosphere at room temperature for 22 hours. After filtration to remove the insoluble materials, the filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2 to chloroform:methanol=10:1) to give 4-(4-ethylbenzyl)-3-methoxy-pyridazine (2.88 g) and 4-(4-ethylbenzyl)-3-methoxy-pyridazine acetate salt (3.32 g).

Workup

  1. filtrationAfter filtration
  2. customto remove the insoluble materials
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2 to chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-2fafe29db2d94770a5aa1b0b7115cf5c
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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