Trimethyl orthovalerate → HCID 22320468, compound

HRID 433191Notes

Reaction equation

HRID 433191 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][CH2:21][CH3:22]>Cl.N1C=CC=CC=1>[CH2:19]([C:18]1[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][Cl: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]=1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 83755Trimethyl orthovalerateHCID 69895270HCID 69895270, compound

Product 1

HCID 22320468HCID 22320468, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 10176127Pyridinium chlorideCatalyst

Procedure

Using the general method of Example 1 Part D, N4-(4-chlorobutyl)quinoline-3,4-diamine (119.1 g, 0.48 mole) was cyclized using trimethyl orthovalerate (93 g, 0.57 mol) in the presence of pyridine hydrochloride (1.1 g, 0.0095 mol) to provide 120 g of 2-butyl-1-(4-chlorobutyl)-1H-imidazo[4,5-c]quinoline as an ivory powder.

Sources & evidence

ORD record
ord-cb2a6e77dec4477ea8221be047d49d19
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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