Water → HCID 19913859, compound

HRID 1110908Notes

Reaction equation

HRID 1110908 reaction equation
Br[CH2:2][C:3]1[CH:15]=[CH:14][C:6]2[C:7](=[O:13])[CH:8]=[C:9]([C:11]#[N:12])[O:10][C:5]=2[CH:4]=1.[Na].[OH:17][C:18]1[CH:19]=[C:20]([CH:33]=[CH:34][CH:35]=1)[O:21][CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1.O>CS(C)=O>[C:11]([C:9]1[O:10][C:5]2[CH:4]=[C:3]([CH2:2][O:17][C:18]3[CH:35]=[CH:34][CH:33]=[C:20]([O:21][CH2:22][C:23]4[CH:32]=[CH:31][C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]=4)[CH:19]=3)[CH:15]=[CH:14][C:6]=2[C:7](=[O:13])[CH:8]=1)#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 10988736Phenol, 3-(2-quinolinylmethoxy)-HCID 14842362HCID 14842362, compound

Product 1

HCID 19913859HCID 19913859, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.5 g of 7-bromomethyl-2-cyano-4-oxo-4H-1-benzopyran and 1.5 g of the sodium salt of 2-(3-hydroxyphenoxy)methylquinoline are combined in 10 ml of dimethylsulfoxide and stirred at room temperature for 5 hours. The mixture is poured into water and extracted with methylene chloride. The organic solution is dried and evaporated. The residue is recrystallized from ethyl acetate/dimethylformamide to give 0.72 g of 2-cyano-7-(3-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic solution is dried
  3. customevaporated
  4. customThe residue is recrystallized from ethyl acetate/dimethylformamide

Sources & evidence

ORD record
ord-8731abb6681e42d88fc0affd4bd887ec
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

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