3-Amino-1-propanol → HCID 15344572, compound

HRID 1452297Notes

Reaction equation

HRID 1452297 reaction equation
[NH2:1][CH2:2][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][CH2:2][NH:1][C:18]([C:17]1[C:10]2[O:9][C:8]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=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 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 13122092HCID 13122092, compound

Product 1

HCID 15344572HCID 15344572, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 7.6 ml of 3-aminopropanol in 50 ml of water was added dropwise over a period of 30 minutes to a suspension of 30 g of 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carbonyl chloride and 15.2 g of potassium carbonate in 400 ml of acetone. The thick suspension was stirred for 3 hours at 20°-25° C. The solvents were removed in vacuo and the residue was taken up in 300 ml of water. After stirring for 1 hour, the precipitate was collected by suction filtration and washed with water. The crude product was purified by crystallization from 95% ethanol and 23.8 g of the title compound were obtained, m.p. 191°-193° C. An additional 4.7 g of the title compound was obtained by concentration in vacuo of the crystallization filtrate.

Workup

  1. customThe solvents were removed in vacuo
  2. stirringAfter stirring for 1 hour
  3. filtrationthe precipitate was collected by suction filtration
  4. washwashed with water
  5. customThe crude product was purified by crystallization from 95% ethanol

Sources & evidence

ORD record
ord-e0827ef8af9f429599ba463e2d793c75
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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