Hydrochloric Acid → 7-((5-Methyl-1H-imidazol-4-yl)methyl)quinoline

HRID 1643392Notes

Reaction equation

[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=O.[OH-].[K+].O.NN.Cl>C(O)CO>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (9) (0.53 g, 2.23 mmol), potassium hydroxide (0.50 g, 8.91 mol), and hydrazine hydrate (0.45 mL, 14.4 mmol) in ethylene glycol was heated at 120° C. for 1 h, then kept at 165° C. overnight. The reaction mixture was cooled to room temperature and acidified with 2 M HCl (aq) to pH˜4. The aqueous layer was washed with chloroform/isoprpanol (3:1, 200 ml). The aqueous layer was basified to pH˜7, and extracted with chloroform/isopropanol (3:1, 200 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 3% saturated ammonia methanol in dichloromethane to give 7-((5-methyl-1H-imidazol-4-yl)methyl)quinoline (10) as a yellow foam (0.32 mg, 1.45 mmol, 65% yield).

Workup

temperatureThe reaction mixture was cooled to room temperature
washThe aqueous layer was washed with chloroform/isoprpanol (3:1, 200 ml)
extractionextracted with chloroform/isopropanol (3:1, 200 mL)
dry with materialThe pooled organic layers were dried over magnesium sulfate
filtrationThe mixture was filtered
customthe solvents were removed under vacuum
customThe residue was purified by chromatography on silica gel with 3% saturated ammonia methanol in dichloromethane

Sources & evidence

ORD record: ord-2ac26afc246141d1a8f6e1cad364c62e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119807B2

Reaction notes

Loading…