2-(Methylamino)ethanol → HCID 19972386, compound

HRID 1452281Notes

Reaction equation

HRID 1452281 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[CH3:6][C:7]1[C:12](=[O:13])[C:11]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18](Cl)=[O:19])[C:10]=2[O:9][C:8]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>O.CC(C)=O>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[C:18]([C:17]1[C:10]2[O:9][C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:7]([CH3:6])[C:12](=[O:13])[C:11]=2[CH:14]=[CH:15][CH:16]=1)=[O:19]

Participants

6

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 11430Potassium CarbonateHCID 13122092HCID 13122092, compound

Product 1

HCID 19972386HCID 19972386, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 1.6 ml of 2-methylamino-ethanol in 10 ml of water was added dropwise over a period of 5 minutes to a suspension of 6 g of 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carbonyl chloride and 1.52 g of potassium carbonate in 60 ml of acetone. After stirring for 2.5 hours at 20°-25° C., the solvent was removed in vacuo and the residue was taken up in 150 ml of acetone. The mixture was refluxed for 15 minutes, and was then filtered. The solvent was evaporated from the filtrate and the residue was dissolved in 20 ml of dimethylformamide, treated with 14 ml of 1.4% aqueous sodium carbonate solution, stirred for 30 minutes at 20°-25° C. and diluted by addition of 150 ml of water. The mixture was extracted with chloroform and the organic layer was washed with 0.5N aqueous hydrochloric acid solution and then with water. The solution was dried over anhydrous sodium sulfate and the chloroform was evaporated off. The resulting oil was taken up in 200 ml of diethyl ether and stirred for 2 hours at 20°-25° C. The solids were collected by filtration and crystallized from ethyl acetate to give 4.97 g of the title compound, m.p. 128°-130° C.

Workup

  1. customthe solvent was removed in vacuo
  2. temperatureThe mixture was refluxed for 15 minutes
  3. filtrationwas then filtered
  4. customThe solvent was evaporated from the filtrate
  5. dissolutionthe residue was dissolved in 20 ml of dimethylformamide
  6. additiontreated with 14 ml of 1.4% aqueous sodium carbonate solution
  7. stirringstirred for 30 minutes at 20°-25° C.
  8. additiondiluted by addition of 150 ml of water
  9. extractionThe mixture was extracted with chloroform
  10. washthe organic layer was washed with 0.5N aqueous hydrochloric acid solution
  11. dry with materialThe solution was dried over anhydrous sodium sulfate
  12. customthe chloroform was evaporated off
  13. stirringstirred for 2 hours at 20°-25° C
  14. filtrationThe solids were collected by filtration
  15. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-64077693420844a5af9c7eab9c25ffc0
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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