Ammonium Chloride → HCID 178486613, compound

HRID 392587Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7]([Li])(C)([CH3:9])[CH3:8].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[CH:20]=[C:19]([CH:26]=[O:27])[CH:18]=[CH:17]2.[Cl-].[NH4+]>C1COCC1.CCCCC>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[CH:20]=[C:19]([C:26]([C:2]1[N:3]=[CH:4][NH:5][CH:6]=1)([OH:27])[CH:7]([CH3:9])[CH3:8])[CH:18]=[CH:17]2

Participants

Conditions

Temperature: -78 °C

Procedure

4-Bromo-1H-imidazol (1.95 g) was dissolved in THF (30 ml) and the mixture was cooled to −78° C. A solution (1.7 M; 20 ml) of t-butyllithium in pentane was added. The mixture was stirred at 0° C. for 1.5 h and again cooled to −78° C. A solution (20 ml) of 6,7-dimethoxy-2-formyl naphthalene (3.32 g) in THF was added and the mixture was warmed from −78° C. to room temperature. The mixture was stirred at room temperature for 16 h and aqueous solution of ammonium chloride was added. The mixture was extracted with ethyl acetate and the organic layer was dried and concentrated. The residue was purified by silica gel column chromatography (eluate, dichloromethane:methanol=10:1) and crystallized from dichloromethane-methanol to give the title compound (1.31 g) as a colorless solid.

Workup

temperatureagain cooled to −78° C
temperaturethe mixture was warmed from −78° C. to room temperature
stirringThe mixture was stirred at room temperature for 16 h
extractionThe mixture was extracted with ethyl acetate
customthe organic layer was dried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (eluate, dichloromethane:methanol=10:1)
customcrystallized from dichloromethane-methanol

Sources & evidence

ORD record: ord-888f94468acc44caba01f1874b675f03
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800778B1

Reaction notes

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