Ethanolamine → HCID 19972514, compound

HRID 2259873Notes

Reaction equation

HRID 2259873 reaction equation
C([BH3-])#N.[Na+].[CH:5]([C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=O.[CH2:25]([CH2:27][NH2:28])[OH:26]>CO.[Cl-].[Zn+2].[Cl-]>[OH:26][CH2:25][CH2:27][NH:28][CH2:5][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 5003444Sodium cyanoborohydrideHCID 19972556HCID 19972556, compound

Product 1

HCID 19972514HCID 19972514, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 2.38 g of anhydrous zinc chloride and 2.30 g of sodium cyanoborohydride in 71 ml of anhydrous methanol was added dropwise under stirring to a mixture of 9.24 g of 8-formyl-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran and 9.12 g of ethanolamine in 90 ml of anhydrous methanol. Stirring was continued at 20°-25° C. for 5 hours, before removal of the solvent in vacuo. 250 ml of water was added to the residue, and the insoluble matter was collected by suction filtration and washed with water. The crude product was dissolved in 1N aqueous acetic acid solution and the solution was washed with ethyl acetate. The aqueous solution was then made alkaline by addition of 2N aqueous sodium hydroxide solution and the precipitate was collected by suction filtration and washed with water to give 8.5 g of the title compound, m.p. 117°-121° C. after drying at 60° C.

Workup

  1. customwas continued at 20°-25° C. for 5 hours, before removal of the solvent in vacuo
  2. addition250 ml of water was added to the residue
  3. filtrationthe insoluble matter was collected by suction filtration
  4. washwashed with water
  5. dissolutionThe crude product was dissolved in 1N aqueous acetic acid solution
  6. washthe solution was washed with ethyl acetate
  7. additionby addition of 2N aqueous sodium hydroxide solution
  8. filtrationthe precipitate was collected by suction filtration
  9. washwashed with water

Sources & evidence

ORD record
ord-29a66977e9bb454d8dd506db753971ef
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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