Triethyl orthoacetate → HCID 22320496, compound

HRID 433196Notes

Reaction equation

HRID 433196 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[NH2:19].[C:20](OCC)(OCC)(OCC)[CH3:21].Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=[C:20]1[CH3:21]

Participants

5

Reactant 3

HCID 66221Triethyl orthoacetateHCID 10176127Pyridinium chlorideHCID 86588278HCID 86588278, compound

Product 1

HCID 22320496HCID 22320496, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

N4-(6-Chlorohexyl)quinoline-3,4-diamine (5 g, 18 mmol), triethyl orthoacetate (2.92 g, 18 mmol), toluene (75 mL), and a catalytic amount of pyridine hydrochloride were combined in a pressure vessel and heated to 140° C. After about 1.5 hours the reaction mixture was allowed to cool and then it was concentrated under reduced pressure to provide 3.8 g of 1-(6-chlorohexyl)-2-methyl-1H-imidazo[4,5-c]quinoline as a dark orange oil.

Workup

  1. temperatureto cool
  2. concentrationit was concentrated under reduced pressure

Sources & evidence

ORD record
ord-97cdcd1072cb4875b072fb128a31bf01
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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