Sodium Bicarbonate → Chromone

HRID 1110901Notes

Reaction equation

HRID 1110901 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 0.71 g of 2-carbopropoxy-6-(3-(quinolin-2-yl-methoxy)benzyloxy)-4-oxo-4H-1-benzopyran and 0.45 g 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 0.55 g 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-9740276942b841aab96679412b4e7dab
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

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