Benzyl Bromide → (8-(Benzyloxy)quinolin-5-yl)methanol

HRID 329906Notes

Reaction equation

HRID 329906 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.[H-].[Na+].[H][H].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.O>[CH2:18]([O:13][C:10]1[CH:11]=[CH:12][C:3]([CH2:2][OH:1])=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:5]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 6757865-(Hydroxymethyl)quinolin-8-olHCID 178418361HCID 178418361, compound

Product 1

HCID 13897639(8-(Benzyloxy)quinolin-5-yl)methanolYield 55.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-(Hydroxymethyl)-8-hydroxyquinoline (1) (6.44 g, 36.75 mmol) was dissolved in dry dimethylformamide (40 ml) and sodium hydride (1.3 g of 80% suspension in mineral oil, corresponding to 1.04 g, 43.3 mmol) was added. The mixture was stirred until hydrogen evolution ceased (~45 min). Benzyl bromide (4.5 ml, 6.47 g, 37.8 mmol) was added and the mixture was stirred for 4 h. The solution was poured into water (350 ml) and stirred for 20 min, and the precipitate was filtered and washed with water. After crystallization from benzene, 5.4 g of product (2) was obtained; mp 192°-194° C. An analytical sample was recrystallized from toluene; Rf 0.68 (chloroform-methanol, 9:1).

Workup

  1. custom(~45 min)
  2. stirringstirred for 20 min
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customAfter crystallization from benzene

Sources & evidence

ORD record
ord-dbd877640e524ff397dfbb6224804378
Source dataset
uspto-grants-1990_01
Patent number
US04894219

Reaction notes

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