Pyridine → HCID 59418674, compound

HRID 2178210Notes

Reaction equation

HRID 2178210 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-f7dde294e25a4340ab88a17ed73d665d
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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