Hydrogen Bromide → HCID 15021170, compound

HRID 1684414Notes

Reaction equation

HRID 1684414 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH2:15])=[CH:6]2.Br.[OH-].[Na+]>>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH2:15])=[CH:6]2

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 15021169HCID 15021169, compound

Product 1

HCID 15021170HCID 15021170, compoundYield 33.4%

Procedure

A mixture of 0.18 g (0.74 mmol) of 3-(6-methoxy-3-quinolyl)alanine and 5.4 mL of 48% hydrobromic acid was stirred at 85°-90° C. overnight. The reaction mixture was cooled to room temperature and neutralized to pH 7.0 with 1N sodium hydroxide solution, then was concentrated under reduced pressure to give a brown solid. After filtration, the solid product was washed with a small amount of cold water and ethyl ether and then was dried in vacuo to give 57.4 mg (33.4%) of the title compound of the formula: ##STR90## NMR (DMSO-d6, CF3COOH) δ 9.05 (1H, bs), 8.9 (1H, bs), 8.2 (1H, d), 7.7 (1H, dd), 7.5 (1H, d), 4.5 (1H, m), 3.5 (2H, m); IR (KBr) ν 3400, 1630, 1500 cm-1.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto give a brown solid
  3. filtrationAfter filtration
  4. washthe solid product was washed with a small amount of cold water and ethyl ether
  5. customwas dried in vacuo

Sources & evidence

ORD record
ord-18f8bc94372542babfa72b93e6170d74
Source dataset
uspto-grants-1997_06
Patent number
US05639885

Reaction notes

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