Hydrogen Bromide → Methyl 2-bromo-3-[7-(5-ethyl-2-pyridylmethoxy)-3-quinolyl]propionate

HRID 1938345Notes

Reaction equation

HRID 1938345 reaction equation
N[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][N:15]=1)[CH:6]=2.[BrH:22].N([O-])=O.[Na+].[C:27]([O:31][CH3:32])(=[O:30])[CH:28]=[CH2:29]>CC(C)=O.CO>[Br:22][CH:28]([CH2:29][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][N:15]=1)[CH:6]=2)[C:27]([O:31][CH3:32])=[O:30]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 7294Methyl AcrylateHCID 214692773-Amino-7-(5-ethyl-2-pyridylmethoxy)quinolineHCID 23668193Sodium Nitrite

Product 1

HCID 21469288Methyl 2-bromo-3-[7-(5-ethyl-2-pyridylmethoxy)-3-quinolyl]propionateYield 75.7%

Reagents, catalysts & solvents 1

HCID 21894497Aceton-methanolSolvent

Procedure

In a mixture of acetone/methanol (5 mL/2 mL) was dissolved 3-amino-7-(5-ethyl-2-pyridylmethoxy)quinoline (680 mg, 2.43 mmol.), and to the resulting solution was added aqueous 47% hydrogen bromide (1.73 g). To the mixture was added aqueous sodium nitrite (189 mg (2.75 mmol.)/0.3 mL) under ice-chilling for 5 minutes, and methyl acrylate (1.33 mL, 14.9 mmol.) was added to the resulting mixture after it was stirred for 20 minutes. Cuprous oxide (23 mg) was added gradually to the mixture kept at 37° C. The mixture was then stirred for one hour at the same temperature. After the completion of reaction was confirmed, the solvent was distilled off under reduced pressure. To the residue were added ethyl acetate and aqueous concentrated ammonia, so that the aqueous phase was made to pH 7. The organic portion was recovered, washed with water, and dried over sodium sulfate. The solvent was distilled off under reduced pressure to give 790 mg of the desired compound as crude residue. The crude residue was subjected to the next step without further purification.

Workup

  1. temperaturechilling for 5 minutes
  2. customkept at 37° C
  3. stirringThe mixture was then stirred for one hour at the same temperature
  4. customAfter the completion of reaction
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo the residue were added ethyl acetate and aqueous concentrated ammonia
  7. customThe organic portion was recovered
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-96dd3928769f43739a57287aebf17402
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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