Water → HCID 19913835, compound

HRID 1090791Notes

Reaction equation

HRID 1090791 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:21][C:22]1[CH:37]=[CH:36][C:25]2[C:26](=[O:35])[CH:27]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:29][C:24]=2[CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:30]([C:28]1[O:29][C:24]2[CH:23]=[C:22]([CH2:21][O:1][C:2]3[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)=[CH:18][CH:19]=3)[CH:37]=[CH:36][C:25]=2[C:26](=[O:35])[CH:27]=1)([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 109887374-[(Quinolin-2-yl)methoxy]phenolHCID 19913882HCID 19913882, compound

Product 1

HCID 19913835HCID 19913835, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

0.8 g of 2-(4-hydroxyphenoxy)methylquinoline, 0.99 g of 7-bromomethyl-2-carboethoxy-4-oxo-4H-1-benzopyran and 0.44 g of potassium carbonate are combined in 15 ml of dimethylformamide and heated at 70° C. for 18 hours. The mixture is poured into water and the aqueous mixture extracted with ethyl acetate. The organic solution is dried and evaporated and the resulting crude product is purified by column chromatography on silica gel to give 0.9 g of 2-carboethoxy-7-(4-(quinolin-2-ylmethoxy)phenoxy-methyl)-4-oxo-4H-1-benzopyran.

Workup

  1. extractionthe aqueous mixture extracted with ethyl acetate
  2. customThe organic solution is dried
  3. customevaporated
  4. customthe resulting crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c8ce73f1110b4237bd3311c94c88b4a0
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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