1,1,1-Trimethoxybutane → HCID 68933325, compound

HRID 521317Notes

Reaction equation

HRID 521317 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[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])[CH3:2].[C:21](OC)(OC)(OC)[CH2:22][CH2:23][CH3:24]>>[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[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:21]1[CH2:22][CH2:23][CH3:24])[CH3:2]

Participants

3

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 86052490HCID 86052490, compound

Product 1

HCID 68933325HCID 68933325, compoundYield 80.6%

Procedure

The general method described in Step 3 of Example 15 was used to cyclize N4-(2,2-diethoxyethyl)quinoline-3,4-diamine (26.5 g, 96.2 mmol) by reaction with trimethyl orthobutyrate (15.9 g, 107 mmol) to provide 1-(2,2-diethoxyethyl)-2-propyl-1H-imidazo[4,5-c]quinoline (25.4 g) as a dark oil that was used directly in the next step without further purification.

Sources & evidence

ORD record
ord-1c9f7300ec7848af87550c0ec6667a40
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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