Dimethylformamide → 8-Quinolinecarboxaldehyde

HRID 2111894Notes

Reaction equation

C([Li])(CC)C.Br[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2.CN(C)[CH:19]=[O:20]>O1CCCC1>[N:15]1[C:16]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[CH:19]=[O:20])[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

sec-Butyllithium (1.4 M in cyclohexane, 5.0 ml, 7.0 mmol) is added dropwise to a stirred solution of 8-bromoquinoline (1.29 g, 6.22 mmol) and anhydrous tetrahydrofuran (22 ml) at −78° C. under nitrogen. The reaction is then stirred at −78° C. for 10 min and then dimethylformamide (2.5 ml, 32.3 mmol) is added. The reaction is then stirred for 10 min at −78° C. and then quenched with water. The reaction is poured into saturated sodium bicarbonate (100 ml) and extracted with ethyl acetate (100 ml×3). The ethyl acetate is dried over sodium sulfate and then the sodium sulfate is filtered. The crude product is concentrated on a rotary evaporator and purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexanes to yield (0.57 g, 58%) of quinoline-8-carboxaldehyde: mass spectrum (ion spray): m/z=158.0 (+1): 1H NMR (CDCl3): δ=11.46 (1H, s), 9.06-9.04 (1H, m), 8.34-8.32 (1H, m), 8.26-8.23 (1H, m), 8.11-8.08 (1H, m), 7.70-7.66 (1H, m), 7.53-7.50 (1H, m).

Workup

stirringThe reaction is then stirred for 10 min at −78° C.
customquenched with water
additionThe reaction is poured into saturated sodium bicarbonate (100 ml)
extractionextracted with ethyl acetate (100 ml×3)
dry with materialThe ethyl acetate is dried over sodium sulfate
filtrationthe sodium sulfate is filtered
concentrationThe crude product is concentrated on a rotary evaporator
custompurified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-92d25d00197a4c8d99922494132c6b75
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521462B2

Reaction notes

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