Hydrochloric Acid → HCID 59371248, compound

HRID 1479713Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]3[CH:15]=[CH:14][CH:13]=[CH:12][C:6]3=[CH:7][CH:8]=2)[N:3]=1.C([Li])CCC.CCCCCC.CN(C)[C:29](=[O:31])[CH3:30].Cl>C1COCC1>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]3[CH:12]=[CH:13][CH:14]=[CH:15][C:5]3=2)[CH:10]=[CH:11][C:2]=1[C:29](=[O:31])[CH3:30]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 2-bromobenzo[h]quinoline (1.52 g, 5.89 mmol) in THF (36 ml) was cooled to −78° C. After 10 minutes a solution of 2.5 M n-butyllithium in n-hexane (2.47 ml, 6.18 mmol) was added. The resulting dark red solution was again stirred at −78° C. for 1 hour after which N,N-dimethylacetamide (0.60 ml, 6.45 mmol) was added drop-wise. The solution was stirred for 1 h at −78° C. and allowed to warm slowly to ambient temperature. A solution of 1 M HCl (7.4 ml, 7.4 mmol) was then added to the organic phase was separated and the aqueous phase was extracted with Et2O (2×15 ml). The organic phases were combined, dried over anhydrous Na2SO4 and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography (petroleum ether/acetate=95/5) to give 1.00 g (77% yield) of 1-(benzo[h]quinolin-2-yl)ethanone in the form of a yellow solid: mp 113-115° C.

Workup

additionwas added drop-wise
temperatureto warm slowly to ambient temperature
customwas separated
extractionthe aqueous phase was extracted with Et2O (2×15 ml)
dry with materialdried over anhydrous Na2SO4
customthe solvent evaporated under reduced pressure
customThe residue was purified by flash chromatography (petroleum ether/acetate=95/5)

Sources & evidence

ORD record: ord-8d6af1198c52499e987d59da59c08936
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409867B2

Reaction notes

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