Sodium Hydroxide → 5-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoic acid

HRID 2366688Notes

Reaction equation

HRID 2366688 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1.[OH-].[Na+]>>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 69506690ethyl 5-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoate

Product 1

HCID 695067285-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoic acidYield 73.5%

Procedure

Ethyl 5-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoate (15.1 g, 42.4 mmol) was treated with sodium hydroxide (2.20 g, 55.2 mmol) according to the method described in Part A of Example 11. The reaction was stirred overnight at ambient temperature to provide 10.2 g of 5-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoic acid after the aqueous work-up procedure.

Sources & evidence

ORD record
ord-8cf19caf349b45348b65d659f4c6b16d
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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