Ethyl orthoformate → HCID 57447041, compound

HRID 2366643Notes

Reaction equation

HRID 2366643 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.[CH:20](OCC)(OCC)OCC>>[N:12]1([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]=[CH:20]1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 68874499HCID 68874499, compound

Product 1

HCID 57447041HCID 57447041, compound

Procedure

The method described in Part A of Example 10 was used to treat ethyl N-(3-aminoquinolin-4-yl)-β-alaninate (10.0 g, 38.6 mmol, prepared in Part A of Example 18) with triethyl orthoformate (8.98 mL, 54.0 mmol). The reaction was complete in three hours. The reaction mixture was filtered to remove a precipitate and then subjected to the work-up procedure to provide 9.7 g of ethyl 3-(1H-imidazo[4,5-c]quinolin-1-yl)propanoate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove a precipitate

Sources & evidence

ORD record
ord-1b4a7258776347f2bdfff6242a073f67
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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