Hydrochloric Acid → N-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide hydrochloride hydrate

HRID 353806Notes

Reaction equation

HRID 353806 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[ClH:28]>C(O)(C)C>[OH2:27].[ClH:28].[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9798928N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide

Product 1

HCID 23512666N-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide hydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide (1 g) was dissolved in isopropanol. Hydrochloric acid (1 eq of 12N) was added. The resulting precipitate was isolated by filtration to provide 1 g of N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide hydrochloride hydrate as a solid, m.p. 254-256° C. Analysis: Calculated for C21H21N5O.HCl.1.5 H2O: % C, 59.63; % H, 5.96; % N, 16.56. Found: % C 59.61; % H, 6.04; % N, 16.64. 1H NMR (500 MHz, DMSO-d6) δ 13.80 (broad s, 1H), 9.15 (broad s, 2H), 8.56 (s, 1H), 8.50 (t, J=6.0 Hz, 1H), 8.23 (d, J=8.0 Hz, 1H), 7.83 (d, J=8.0 Hz, 1H), 7.76 (d, J=8.0 Hz, 2H), 7.71 (t, J=8.0 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 7.50 (t, J=8.0 Hz, 1H), 7.42 (t, J=8.0 Hz, 2H), 4.72 (t, J=7.0 Hz, 2H), 3.30 (q, J=7.0 Hz, 2H), 1.93 (quintet, J=7.0 Hz, 2H), 1.61 (quintet, J=7.0 Hz, 2H).

Workup

  1. customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-7ed0f66df3284e8087d81888bbc69ea3
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

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