3-Hydroxybenzaldehyde → 3-[(7-Chloro-2-quinolinyl)methoxy]benzaldehyde

HRID 258464Notes

Reaction equation

HRID 258464 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12]Br)=[N:9]2)=[CH:4][CH:3]=1.[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CC(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[CH:18]=[O:19])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 102441602-(Bromomethyl)-7-chloroquinoline

Product 1

HCID 190028993-[(7-Chloro-2-quinolinyl)methoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 7-chloro-2-(bromomethyl)quinoline (50.5 g, 197 mmol, EP 233,763, Example 4, Step 1), 3-hydroxybenzaldehyde (22.9 g, 188 mmol) and K2CO3 (51.7 g, 375 mmol) in 600 mL of acetone was heated to reflux for 2 h. After cooling down, 200 mL of CH2Cl2 was added and the mixture was filtered through celite with acetone:CH2Cl2 3:1. The title product was purified by flash chromatography on silica with EtOAc:toluene 5:95 to yield 46.64 g, 83%. (Alternatively, the product may be purified by a swish in ether:hexane 7:1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. temperatureAfter cooling down
  4. filtrationthe mixture was filtered through celite with acetone:CH2Cl2 3:1
  5. customThe title product was purified by flash chromatography on silica with EtOAc:toluene 5:95
  6. customto yield 46.64 g, 83%
  7. custom(Alternatively, the product may be purified by a swish in ether:hexane 7:1)

Sources & evidence

ORD record
ord-6fd4d79c2c1043678766d7ed13aa47e3
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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