Water → HCID 178515619, compound

HRID 1790852Notes

Reaction equation

HRID 1790852 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.O>CN(C=O)C>[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 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178515617HCID 178515617, compound

Product 1

HCID 178515619HCID 178515619, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

2,8-Quinolinediol (133.3 g, 0.827 mol) was dissolved in 800 mL of anhydrous DMF under an atmosphere of dry N2. To this solution was added potassium carbonate (183 g, 1.32 mol) followed by benzyl bromide (110 mL, 0.909 mol) and the solution was then warmed up to 65° C. and reacted at this temperature overnight. The reaction mixture was then poured into 9 L of water and the resulting solution was stirred at ambient temperature for 5.5 hours after which time it was filtered. The solid was washed with water, collected and suspended in toluene and finally the solution was concentrated under vacuum to give 142 g of 8-benzyloxy-quinolin-2-ol. This material (142 g, 0.565 mol) was dissolved in 500 mL of DCE under an atmosphere of dry N2. Oxalyl chloride (99 mL, 1.13 mol) was added dropwise to this solution followed by 1 mL of DMF. After the addition was complete, the reaction was stirred at ambient temperature for 30 minutes after which time the reaction was warmed to 84° C. The reaction mixture was stirred at this temperature for 10 hours and then concentrated under vacuum. The resulting residue was partitioned between DCM and aqueous saturated NaHCO3. The DCM layer was washed again with aqueous saturated NaHCO3, dried over Na2SO4, filtered and concentrated under vacuum to give a brown solid. The solid was recrystallised from toluene to give two crops of (68.3 g and 38.3 g) of 8-benzyloxy-2-chloro-quinoline.

Workup

  1. customreacted at this temperature overnight
  2. filtrationwas filtered
  3. washThe solid was washed with water
  4. customcollected
  5. concentrationfinally the solution was concentrated under vacuum

Sources & evidence

ORD record
ord-c4b7982cbe3b48a4b252de5aac9e76dd
Source dataset
uspto-grants-2006_07
Patent number
US07071337B2

Reaction notes

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