1,1,1-Trimethoxypropane → HCID 22320470, compound

HRID 433192Notes

Reaction equation

HRID 433192 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][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

4

Reactant 3

HCID 1411451,1,1-TrimethoxypropaneHCID 10176127Pyridinium chlorideHCID 69895270HCID 69895270, compound

Product 1

HCID 22320470HCID 22320470, compoundYield 72.7%

Procedure

Using the general method of Example 1 Part D, N4-(4-chlorobutyl)quinoline-3,4-diamine (30 g, 0.12 mole) was cyclized using trimethyl orthopropionate (23.3 g, 0.13 mol) in the presence of a catalytic amount of pyridine hydrochloride to provide 25.1 g of 1-(4-chlorobutyl)-2-ethyl-1H-imidazo[4,5-c]quinoline as solid.

Sources & evidence

ORD record
ord-b0e92f2fdffc4f688bc39977ffd1cdcf
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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