Hydrochloric Acid → (1H-Imidazol-4-yl)-(6-methoxynaphthalen-2-yl)-(pyridin-3-yl)methanol

HRID 1368515Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1)([C:15]1[N:16]=[CH:17][N:18](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:19]=1)[OH:14])[CH:7]=[CH:6]2.Cl>C(O)=O>[NH:18]1[CH:19]=[C:15]([C:13]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)[OH:14])[N:16]=[CH:17]1

Participants

Conditions

Temperature: 50 °C

Procedure

(6-Methoxynaphthalen-2-yl)-(pyridin-3-yl)-(1-trityl-1H-imidazol-4-yl)methanol (0.80 g) was dissolved in 90% solution of formic acid (3 ml), and the solution was stirred at 50° C. for 30 min. To the solution was added 1 N-hydrochloric acid, and precipitate was filtered off. The filtrate was washed with ether, and neutralized with potassium carbonate. The filtrate was extracted with chloroform and concentrated. The residue was purified by silica gel column chromatography (eluent, chloroform:methanol=5:1). Recrystallization from THF gave the titled compound (0.36 g) as a colorless powder.

Workup

filtrationwas filtered off
washThe filtrate was washed with ether
extractionThe filtrate was extracted with chloroform
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (eluent, chloroform:methanol=5:1)
customRecrystallization from THF

Sources & evidence

ORD record: ord-6a4ef641a44d4f63a46e9df6d9c23f94
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573289B1

Reaction notes

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