Triethyl orthoacetate → HCID 57447045, compound

HRID 2366674Notes

Reaction equation

HRID 2366674 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](OCC)(OCC)(OCC)[CH3:21]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH3:20][C:21]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

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 68874499HCID 68874499, compound

Product 1

HCID 57447045HCID 57447045, compoundYield 61.5%

Reagents, catalysts & solvents 1

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

Procedure

Ethyl N-(3-aminoquinolin-4-yl)-β-alaninate (9.0 g, 35 mmol) was treated with triethyl orthoacetate (8.91 mL, 48.6 mmol) and pyridinium p-toluenesulfonate (0.200 g) according to the method described in Part A of Example 10 to provide 6.10 g of ethyl 3-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propanoate. The reaction was complete in two hours, and a precipitate was removed by filtration from the organic layer during the work-up procedure.

Sources & evidence

ORD record
ord-d8b5139b33604364b8cb825d5e1f42d0
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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