1,1,1-Trimethoxybutane → HCID 22320537, compound

HRID 433185Notes

Reaction equation

HRID 433185 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[NH2:17].[C:18](OC)(OC)(OC)[CH2:19][CH2:20][CH3:21]>Cl.N1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=[C:18]1[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 69895270HCID 69895270, compound

Product 1

HCID 22320537HCID 22320537, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 10176127Pyridinium chlorideCatalyst

Procedure

Using the general method of Example 1 Part D, N4-(4-chlorobutyl)quinoline-3,4-diamine (˜21.45 mmol) was cyclized using trimethyl orthobutyrate (3.8 g, 25.74 mmol) in the presence of pyridine hydrochloride (0.1 g). The crude product was purified by chromatography (silica gel eluting with 95/5 dichloromethane/methanol) to provide 3.6 g of 1-(4-chlorobutyl)-2-propyl-1H-imidazo[4,5-c]quinoline as a light green oil which slowly solidified.

Workup

  1. customThe crude product was purified by chromatography (silica gel eluting with 95/5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-7f691507ed154e7cad3946ecbf68cefe
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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