Isoamyl Nitrite → 3-Chloro-5-[4-(methoxymethoxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazole

HRID 351201Notes

Reaction equation

HRID 351201 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:14]=[C:13](N)[CH:12]=2)=[CH:7][CH:6]=1.[Cl-:25].[Li+].N(OCCC(C)C)=O>C(#N)C.[Cu](Cl)Cl>[Cl:25][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=2)[N:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:14]=1

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 433294Lithium ChlorideHCID 210910035-[4-(Methoxymethoxy)phenyl]-1-(4-methoxyphenyl)-1H-pyrazol-3-amine

Product 1

HCID 210908613-Chloro-5-[4-(methoxymethoxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-[4-(methoxymethoxy)phenyl]-1-(4-methoxyphenyl)-1H-pyrazol-3-amine obtained by Example 20-2 (3.79 g), lithium chloride (2.47 g), and copper (II) chloride (3.13 g) in acetonitrile (60 ml) was stirred at room temperature for 10 min. To this mixture was added isoamyl nitrite (2.73 g), and the mixture was stirred at room temperature for 1 hr.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr

Sources & evidence

ORD record
ord-609e667e53024d199962f464f539e5cc
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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