Hydrochloric Acid → 6-(2-Imidazole-1-yl-ethoxy)-2-pyridin-2-ylmethylene-3,4-dihydro-2H-naphthalen-1-one

HRID 368300Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[N:9]1([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[C:23](=[O:27])[CH2:22][CH2:21][CH2:20]3)[CH:13]=[CH:12][N:11]=[CH:10]1.Cl.C([O-])(O)=O.[Na+]>N1CCCCC1.C(O)(=O)C>[N:9]1([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[C:23](=[O:27])[C:22](=[CH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:21][CH2:20]3)[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

Conditions

Temperature: 130 °C

Procedure

2-Pyridine carboxaldehyde (0.202 g, 1.9 mmol) was added to a mixture of 6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (1) (0.322 g, 1.2 mmol) in piperidine:acetic acid (30 μL:24 μL). The reaction mixture was heated in a 130° C. oil bath with efficient stirring for 1.5 hours. After cooling to room temperature, 2 mL of 1N HCl was added and the mixture stirred overnight. The mixture was made neutral with the addition of a saturated solution of NaHCO3 and then extracted into DCM (3×50 mL). The pooled extracts were washed sequentially several times with water, then brine, dried, filtered, and concentrated in vacuo to leave a dark brown oil. Purification by flash chromatography (silica gel, 135 g, 7% MeOH in DCM) afforded 0.075 g of the title compound as a light tan solid.

Workup

temperatureAfter cooling to room temperature
stirringthe mixture stirred overnight
extractionextracted into DCM (3×50 mL)
washThe pooled extracts were washed sequentially several times with water
dry with materialbrine, dried
filtrationfiltered
concentrationconcentrated in vacuo
customto leave a dark brown oil
customPurification by flash chromatography (silica gel, 135 g, 7% MeOH in DCM)

Sources & evidence

ORD record: ord-e9272fc3d6cf4d829ff1692a50833b89
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133303

Reaction notes

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