Water → HCID 69893205, compound

HRID 392148

Reaction equation

HRID 392148 reaction equation
[Br:1][C:2]1[C:11](O)=[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.[OH2:33]>CC(N(C)C)=O>[CH2:19]([O:18][CH2:14][C@H:15]([OH:17])[CH2:16][O:33][C:5]1[C:6]([CH3:13])=[N:7][C:8]2[C:3]([CH:4]=1)=[C:2]([Br:1])[CH:11]=[CH:10][CH:9]=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 69893205HCID 69893205, compoundYield 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. Rf=0.35 (ethyl acetate); 1H NMR (DMSO) δ 8.31 (d, J=8.8 Hz, 1H), 7.96 (d, J=9.2 Hz, 1H), 7.72 (d, J=9.3 Hz, 1H), 7.74 (d, J=8.7 Hz, 1H), 7.25-7.36 (m, 5H), 5.28 (d, J=5.1 Hz, 1H), 4.56 (s, 2H), 4.22-4.29 (m, 2H), 4.08-4.15 (m, 1H), 3.61-3.73 (m, 2H), 2.66 (s, 3H); Specific rotation=+6.2° (c=1, CH3OH);

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-b5f3061ee84d473db5f32660ffa15eb2
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Linked notes

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