Hydroxyamine hydrochloride → HCID 72448486, compound

HRID 1623171Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:21][O:22][CH2:23][CH3:24])[N:14]([CH2:15][CH2:16][CH2:17][C:18](=O)[CH3:19])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.[NH2:26][OH:27]>>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:21][O:22][CH2:23][CH3:24])[N:14]([CH2:15][CH2:16][CH2:17][C:18](=[N:26][OH:27])[CH3:19])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 58837337HCID 58837337, compound

Product 1

HCID 72448486HCID 72448486, compound

Procedure

By the general method described in Part F of Example 30, 5-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one was reacted with hydroxylamine hydrochloride to provide 5-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one oxime in about a 3.5 to 1 mixture of E and Z isomers as a white solid after recrystallization from a mixture of toluene and methanol, mp 220-223° C.

Sources & evidence

ORD record: ord-cd1c2fe5f1704a59a26088397578a593
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778963B2

Reaction notes

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