Sodium Bicarbonate → Chromone

HRID 1090780Notes

Reaction equation

HRID 1090780 reaction equation
C([C:7]1[O:8][C:9]2[CH:17]=[CH:16][C:15](OCC3C=CC=C(OCC4C=CC5C(=CC=CC=5)N=4)C=3)=[CH:14][C:10]=2[C:11](=[O:13])[CH:12]=1)(OCCC)=O.C(=O)(O)[O-].[Na+]>C(O)C.O>[O:13]=[C:11]1[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[O:8][CH:7]=[CH:12]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 199138482-carbopropoxy-6-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H1-benzopyran

Product 1

HCID 10286Chromone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.71g of 2-carbopropoxy-6-(3-(quinolin-2-yl-methoxy)benzyloxy)-4-oxo-4H-1-benzopyran and 0.45g of sodium bicarbonate in 20 ml of ethanol in 20 ml of water is refluxed for 1.5 hours, then stirred at room temperature overnight. The mixture was neutralized and the resulting solid is filtered off, washed with water and dried in vacuo to give 0.55g of 2-carboxy-6-(3-quinolin-2- ylmethoxy)benzyloxy)-4-oxo-4H-1-benzopyran as a light yellow solid having an m.p. of 253°-54° C.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. filtrationthe resulting solid is filtered off
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1ee73434b9db4f5289f5098d1b7d2d95
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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