Water → 6-Bromo-2-methoxycarbonylmethyltetrahydroquinoline

HRID 862562Notes

Reaction equation

HRID 862562 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1)=[O:4].[Br:16]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:15][CH2:14]2

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 103529122-Quinolineacetic acid, 1,2,3,4-tetrahydro-, methyl ester

Product 1

HCID 104016006-Bromo-2-methoxycarbonylmethyltetrahydroquinolineYield 102.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-methoxycarbonylmethyltetrahydroquinoline (31.5 g, 0.153 mol) in DMF (750 mL) was added dropwise a solution of N-bromosuccinimide (27.41 g, 0.154 mol) in DMF (550 mL) at 0° C. The mixture was stirred for 2 h at the same temperature, poured into water (2 L), and extracted with a mixture of toluene and ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to give 44.72 g of the title compound (quant).

Workup

  1. extractionextracted with a mixture of toluene and ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74a3160a20d244eaa71577e96b4e0e55
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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