Sodium Chloride → HCID 10505429, compound

HRID 861317Notes

Reaction equation

HRID 861317 reaction equation
O[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.[C:29](=[O:32])([O-])[O-].[Cs+].[Cs+].[Na+].[Cl-]>CN(C=O)C>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([O:32][CH2:29][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 203942-(Chloromethyl)quinolineHCID 691504,4'-Dihydroxybenzophenone

Product 1

HCID 10505429HCID 10505429, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,4'-dihydroxybenzophenone (12.4 g, 57.9 mmol), 2-chloromethylquinoline (23.4 g, 132 mmol) and cesium carbonate (46.0 g, 141.2 mmol) was stirred in dry DMF (170 mL). After 5 hours, saturated aqueous NaCl was added and the light brown solid formed was collected by filtration and washed with water. The solid was suspended in ether and collected by filtration, resuspended in ethanol and collected again by filtration and dried in vacuo to afford bis(4-(2-quinolylmethoxy)phenyl) ketone (27.3 g, 95%): IR (KBr) 1635, 1600, 1505, 1250 cm-1 ; 1H NMR (300 MHz, DMSO-d6)δ5.48 (s, 4H), 7.22 (d, 4H, J=9 Hz), 7.64 (m, 2H), 7.71 (d, 4H, J=9 Hz), 7.80 (m, 2H), 8.02 (m, 2H), 8.44 (d, 2H, J=8.5 Hz); MS (DCI/NH3) m/e: 497 (M+H)+.

Workup

  1. customthe light brown solid formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. filtrationcollected by filtration
  5. filtrationcollected again by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2a783211847b46228fc505bfbb90fbf1
Source dataset
uspto-grants-1998_02
Patent number
US05714488

Reaction notes

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