1,1,1-Trimethoxybutane → HCID 22320418, compound

HRID 433190Notes

Reaction equation

HRID 433190 reaction equation
[CH3:1][S: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](OC)(OC)(OC)[CH2:18][CH2:19][CH3:20].Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][S: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][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 1235121,1,1-TrimethoxybutaneHCID 10176127Pyridinium chlorideHCID 69851340HCID 69851340, compound

Product 1

HCID 22320418HCID 22320418, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

N4-[2-(Methylthio)ethyl]quinoline-3,4-diamine (4.2 g, 19.2 mmol), trimethyl orthobutyrate (2.86 g, 19.2 mmol), pyridine hydrochloride (catalytic amount) and toluene were combined in a pressure vessel and heated at 140° C. for 1 hour. The reaction mixture was allowed to cool and then it was concentrated under reduced pressure to provide 4.9 g of 1-[2-(methylthio)ethyl]-2-propyl-1H-imidazo[4,5-c]quinoline.

Workup

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

Sources & evidence

ORD record
ord-fea893d07eab4b968300a2af429b38f4
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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