Pyridine → HCID 59418674, compound

HRID 1641047Notes

Reaction equation

HRID 1641047 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[C:12](=[O:14])[CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 7918Acetic Anhydride2×HCID 138650477-Bromo-1,2,3,4-tetrahydroquinoline

Product 1

HCID 59418674HCID 59418674, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 7-bromo-1,2,3,4-tetrahydroquinoline (1E) (1.0 g, 4.7 mmol) in DCM (30 mL) was added TEA (1.6 mL, 12 mmol), acetic anhydride (1.1 mL, 12 mmol), and pyridine (1.0 mL, 10.0 mmol). The reaction was allowed to stir at rt for 24 hours while monitoring by LCMS. To the reaction mixture was added TEA (1.6 mL, 12 mmol), acetic anhydride (1.1 mL, 12.0 mmol), and pyridine (1.0 mL, 10 mmol). The reaction was allowed to stir at rt for 24 hours. The reaction mixture was concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel eluting with a gradient of 0 to 100% EtOAc in hexanes to provide 1.09 g (91%) of the desired product 1-(7-bromo-3,4-dihydroquinolin-1(2H)-yl)ethanone (1F): LC/MS (APCI): m/z 255.7 (M+H).

Workup

  1. stirringto stir at rt for 24 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe crude residue was purified by column chromatography on silica gel eluting with a gradient of 0 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-11b26ae4b83346a6b47096e68d5d43e5
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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