Dimethylformamide → 2-Oxo-1,2,3,4-tetrahydroquinoline-5-carbaldehyde

HRID 856998Notes

Reaction equation

HRID 856998 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C([Li])CCC.CCCCCCC.CN([CH:28]=[O:29])C>CC(O)=O.C1COCC1>[CH:28]([C:3]1[CH:2]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:12])[NH:8]2)=[O:29]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8900HeptaneHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-oneHCID 178418339Butyllithium

Product 1

HCID 112753262-Oxo-1,2,3,4-tetrahydroquinoline-5-carbaldehydeYield 14%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Following the procedure reported above for 2-ethyl-5-formyl-2H-1,2,3,4-tetrahydroisoquinolone described above, 6-bromo-1,2,3,4-tetrahydroquinol-2-one (1.07 g, 4.73 mmol), a solution oft-butyllithium in heptane (1.7M, 9.7 mL, 16.6 mmol), DMF (0.37 mL, 4.73 mmol) and THF 35 mL) were combined. The reaction mixture was stirred at −78° C. for 4 h and HOAc (1 mL) was added. The previously described workup provided crude product. Column chromatography (EtOAc:hexane::1:1, then DCM:MeOH::97:3) and removal of solvent in vacuo provided a white solid (116 mg, 14% yield): 1H NMR: 9.90 (s, 1H), 8.0 (s, 1H), 7.77–7.74 (m, 2H), 6.89 (d, 1H, J=8), 3.07 (t, 2H, J=7), 2.71 (t, 2H, J=7).

Workup

  1. customThe previously described workup provided crude product
  2. customColumn chromatography (EtOAc:hexane::1:1, then DCM:MeOH::97:3) and removal of solvent in vacuo

Sources & evidence

ORD record
ord-1001bebd20714450ad7dee976d9d642a
Source dataset
uspto-grants-2006_12
Patent number
US07144894B2

Reaction notes

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