Dimethylformamide → HCID 178515619, compound

HRID 1095722Notes

Reaction equation

HRID 1095722 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][C:2]=1[OH:12].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CN(C=O)C>O>[CH2:19]([O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[C:2]([OH:12])[CH:3]=[CH:4]2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178515617HCID 178515617, compound

Product 1

HCID 178515619HCID 178515619, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A flask was charged with quinoline-2,8-diol (20.0 g, 124.1 mmol), K2CO3 (17.15 g, 124.1 mmol), benzyl bromide (14.76 ml, 124.1 mmol) and DMF (124.1 ml, 124.1 mmol). The resulting mixture was heated to 65° C. overnight, then poured into 1000 ml water and stirred for 5 hours. The solids were filtered and washed with 1000 ml diethyl ether to yield 26.5 g (85% yield) of desired product.

Workup

  1. filtrationThe solids were filtered
  2. washwashed with 1000 ml diethyl ether

Sources & evidence

ORD record
ord-3ff1d0a58a47448baaaefc832598ab40
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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