Water → (2s)-1-(Benzyloxy)-3-[(5-bromo-2-methyl-6-quinolinyl)oxy]-2-propanol

HRID 2120986Notes

Reaction equation

HRID 2120986 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2.[CH2:14]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@@H:15]1[O:17][CH2:16]1.C(N(CC)CC)C.O>CC(N(C)C)=O>[CH2:19]([O:18][CH2:14][C@H:15]([OH:17])[CH2:16][O:12][C:11]1[C:2]([Br:1])=[C:3]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6]([CH3:13])[CH:5]=[CH:4]2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 159746(-)-Benzyl (R)-glycidyl etherHCID 112301385-Bromo-2-methylquinolin-6-ol

Product 1

HCID 11361638(2s)-1-(Benzyloxy)-3-[(5-bromo-2-methyl-6-quinolinyl)oxy]-2-propanolYield 73%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 5-bromo-2-methyl-6-quinolinol (30.1 g, 126 mmol), (R)-benzyl glycidyl ether (24.9 g, 152 mmol) and triethylamine (17.4 g, 172 mmol) in DMA (200 mL) was heated in a 95-98° C. oil bath for 2 days. The solution was cooled and poured into water (300 mL) while stirring. The tan precipitate formed was filtered, washed with water (100 mL) and dried in a vacuum oven to give 37 g (73%) of the title compound as a tan solid.

Workup

  1. temperatureThe solution was cooled
  2. customThe tan precipitate formed
  3. filtrationwas filtered
  4. washwashed with water (100 mL)
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-9f9baf42ca124a218e46d6d0d539556f
Source dataset
uspto-grants-2004_02
Patent number
US06693197B2

Reaction notes

Loading…