Ethyl orthopropionate → HCID 22320470, compound

HRID 433184Notes

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](OCC)(OCC)(OCC)[CH2:19][CH3:20].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][CH3:20]

Participants

Reactant 3

HCID 66995Ethyl orthopropionate

HCID 10176127Pyridinium chloride

HCID 69895270HCID 69895270, compound

Product 1

HCID 22320470HCID 22320470, compoundYield 72.9%

Procedure

Using the general method of Example 1 Part D, N4-(4-chlorobutyl)quinoline-3,4-diamine (˜35.75 mmol) was cyclized using triethyl orthopropionate (7.56 g, 42.9 mmol) in the presence of pyridine hydrochloride (0.41 g). The crude product was purified by chromatography (silica gel eluting with 95/5 dichloromethane/methanol) to provide 7.5 g of 1-(4-chlorobutyl)-2-ethyl-1H-imidazo[4,5-c]quinoline as a white powder.

Workup

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

Sources & evidence

ORD record: ord-5c36c47e9a624113a7d181bd3f80ce2f
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667312B2

Reaction notes

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