1,1,1-Trimethoxybutane → HCID 57447034, compound

HRID 2366631Notes

Reaction equation

HRID 2366631 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:20](OC)(OC)(OC)[CH2:21][CH2:22][CH3:23]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:21]([C:20]1[N:12]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 68874499HCID 68874499, compound

Product 1

HCID 57447034HCID 57447034, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)Catalyst

Procedure

Ethyl N-(3-aminoquinolin-4-yl)-β-alaninate (33.3 g, 128 mmol) was treated according to a modification of the method described in Part B of Example 8. After the addition of trimethyl orthobutyrate (25.6 mL, 161 mmol) and pyridinium p-toluenesulfonate (0.200 g, 0.796 mmol), the reaction was heated at reflux for two hours and subjected to the work-up procedure to provide 37.1 g of ethyl 3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propanoate, which was used without purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for two hours

Sources & evidence

ORD record
ord-3632a2d6ced849b09818a958c09a5046
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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