Water → HCID 13066476, compound

HRID 1283124Notes

Reaction equation

HRID 1283124 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH2:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12.O.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23]Cl>[Na].C(O)(C)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH:15]([CH2:23][CH2:22][N:21]([CH3:25])[CH3:20])[C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12

Participants

6

Reactant 3

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 13066473HCID 13066473, compound

Product 1

HCID 13066476HCID 13066476, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 5360545SodiumSolvent

Procedure

4.1 g of 5H-[1]benzopyrano[2,3-b]pyridin-7-yl-acetone is dissolved in a solution of 0.44 g of metallic sodium in 20 ml of absolute isopropyl alcohol by warming to 50°-60°C. The solution is water-cooled, 2.3 g of 2-dimethylaminoethyl chloride is added, and the mixture is stirred under reflux for 1 hour. The reaction mixture is concentrated, chloroform and water are added to the residue, and the mixture is shaken. The chloroform layer is separated and extracted with dilute hydrochloric acid, and the extract is neutralized with 10% sodium hydroxide and then extracted with chloroform. The chloroform extract is washed with water, dried over anhydrous magnesium sulfate and concentrated to give 3 g of crude 3-(5H-[1]benzopyrano[2,3-b]-pyridin-7-yl)-5-dimethylamino-2-pentanone as a pale yellowish brown transparent oil. The product is treated with maleic acid in acetone in a conventional manner, and the crystalline precipitate is recrystallized from isopropyl alcohol to give 3-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-5-dimethylamino-2-pentanone maleate as white needles melting at 145°-146°C.

Workup

  1. temperatureby warming to 50°-60°C
  2. temperaturecooled
  3. temperatureunder reflux for 1 hour
  4. concentrationThe reaction mixture is concentrated
  5. additionchloroform and water are added to the residue
  6. stirringthe mixture is shaken
  7. customThe chloroform layer is separated
  8. extractionextracted with dilute hydrochloric acid
  9. extractionextracted with chloroform
  10. extractionThe chloroform extract
  11. washis washed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-874a56af3f34446aabba3550042c1204
Source dataset
uspto-grants-1976_08
Patent number
US03974168

Reaction notes

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