Ethyl orthopropionate → HCID 22320441, compound

HRID 433182Notes

Reaction equation

HRID 433182 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[NH2:16].[C:17](OCC)(OCC)(OCC)[CH2:18][CH3:19].Cl.N1C=CC=CC=1>>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=[C:17]1[CH2:18][CH3:19]

Participants

4

Reactant 3

HCID 66995Ethyl orthopropionateHCID 10176127Pyridinium chlorideHCID 18760238HCID 18760238, compound

Product 1

HCID 22320441HCID 22320441, compoundYield 71.2%

Procedure

Using the general method of Example 1 Part D, N4-(3-chloropropyl)quinoline-3,4-diamine (˜37.6 mmol) was cyclized using triethyl orthopropionate (7.96 g, 45.2 mmol) in the presence of pyridine hydrochloride (0.43 g). The crude product was purified by chromatography (silica gel eluting with 95/5 dichloromethane/methanol) to provide 7.33 g of 1-(3-chloropropyl)-2-ethyl-1H-imidazo[4,5-c]quinoline as a white solid.

Workup

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

Sources & evidence

ORD record
ord-d3bab1b83be44cc8ae844ac9987ea9d9
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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