Potassium Iodide → HCID 19913858, compound

HRID 1090784Notes

Reaction equation

HRID 1090784 reaction equation
Cl[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.[C:21]([C:27]1[O:28][C:29]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([OH:39])[C:30]=2[C:31](=[O:33])[CH:32]=1)([O:23][CH2:24][CH2:25][CH3:26])=[O:22].[I-].[K+]>CC(C)=O.CN(C)C=O>[C:21]([C:27]1[O:28][C:29]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([O:39][CH2:2][C:3]3[CH:20]=[CH:19][C:6]([O:7][CH2:8][C:9]4[CH:18]=[CH:17][C:16]5[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=5)[N:10]=4)=[CH:5][CH:4]=3)[C:30]=2[C:31](=[O:33])[CH:32]=1)([O:23][CH2:24][CH2:25][CH3:26])=[O:22]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 147741632-(4-Chloromethylphenoxy)methylquinolineHCID 19913868HCID 19913868, compound

Product 1

HCID 19913858HCID 19913858, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

0.78 g of 2-(4-chloromethylphenoxy)methylquinoline, 0.76 g of 2-carbopropoxy-6-chloro-5-hydroxy-4-oxo-4H-1-benzopyran and a catalytic amount of potassium iodide are combined in 50 ml of acetone and 2 ml of dimethylformamide, and refluxed for 19 hours. The crude solid obtained on cooling is purified by flash chromatography to give 2-carbopropoxy-6-chloro-5-(4-(quinolin-2-ylmethoxy)benzyloxy) 4-oxo-4H-1-benzopyran having an m.p. of 173°-74° C.

Workup

  1. customThe crude solid obtained
  2. temperatureon cooling
  3. customis purified by flash chromatography

Sources & evidence

ORD record
ord-45ebf63c475c4eb680b5b89e419100eb
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

Loading…