Pyridine → Isocromil

HRID 26223Notes

Reaction equation

HRID 26223 reaction equation
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[C:7]1[O:8][C:9]2[C:14]([C:15](=[O:17])[CH:16]=1)=[CH:13][C:12]([C:18](Cl)=[O:19])=[CH:11][CH:10]=2)([CH3:3])[CH3:2].[OH:25]CCN1CCOCC1.N1C=CC=CC=1>C1C=CC=CC=1>[C:18]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([C:6]1[CH:21]=[CH:22][CH:23]=[CH:24][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2])=[CH:16][C:15]2=[O:17])([OH:25])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 611632-MorpholinoethanolHCID 213250372'-Isopropoxy-flavone-6-carbonyl-chloride

Product 1

HCID 9973510IsocromilYield 88.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2'-isopropoxy-flavone-6-carbonyl-chloride (4.3 g) prepared according to Example 18, dissolved in anhydrous benzene (40 ml) was treated with N-hydroxyethyl-morpholine (3.2 g) and pyridine (1 ml) at room temperature for 24 hours. The benzene solution was washed with aqueous citric acid 40% with sodium bicarbonate and water, then evaporated to dryness. The residue, crystallised from acetone, gave morpholinoethyl-ester of 6-carboxy-2'-isopropoxy-flavone (3.6 g; m.p. 133°-135° C.).

Workup

  1. washThe benzene solution was washed with aqueous citric acid 40% with sodium bicarbonate and water
  2. customevaporated to dryness
  3. customThe residue, crystallised from acetone

Sources & evidence

ORD record
ord-d5dc2228dafd40e4b3dca36c78210c5d
Source dataset
uspto-grants-1979_04
Patent number
US04148900

Reaction notes

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