Phenyltrimethylammonium bromide dibromide → HCID 58495428, compound

HRID 516259Notes

Reaction equation

HRID 516259 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[Br-:18].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C)(C)C1C=CC=CC=1.C[N+](C)(C)C1C=CC=CC=1>ClCCl.CO>[Br:18][C:17]1[C:2]([OH:1])=[CH:3][C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=2[CH:16]=1

Participants

5

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 584953637-Hydroxy-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester

Product 1

HCID 58495428HCID 58495428, compoundYield 171%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, to a mixed solution of 5.0 g of ethyl 7-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate in 100 ml of dichloromethane and 20 ml of methanol was added portionwise 8.05 g of N,N,N-trimethylanilinium tribromide under ice-cooling, followed by stirring at the same temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, the residue was extracted by the addition of ethyl acetate and water, and the organic layer was washed with 1 M aqueous hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure to obtain 6.67 g of ethyl 7-bromo-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate as a beige solid.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe residue was extracted by the addition of ethyl acetate and water
  4. washthe organic layer was washed with 1 M aqueous hydrochloric acid and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f24c1da8e61b4a078f432902741e612c
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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