Chloroacetone → HCID 12899701, compound

HRID 1680814Notes

Reaction equation

HRID 1680814 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:11]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]=3[C:17](=[O:19])[O:18][C:5]=2[CH:4]=1.Cl[CH2:21][C:22](=[O:24])[CH3:23].C(N(CC)CC)C>C(O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:11]3[CH2:16][CH2:15][N:14]([CH2:21][C:22]([CH3:23])=[O:24])[CH2:13][C:12]=3[C:17](=[O:19])[O:18][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 108252898,9-dimethoxy-1,2,3,4-tetrahydro-5H-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 12899701HCID 12899701, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 26.1 g (0.1 m) of 1,2,3,4-tetrahydro-8,9-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridine-5-one, prepared in Example 1, 13 g (0.14 m) of chloroacetone, and 14.2 g (0.14 m) of triethylamine in 450 ml of ethanol was refluxed overnight. After evaporation, the residue was partitioned between dilute NaOH solution and CHCl3. After drying (Na2SO4) and evaporation of the CHCl3 extract, the residue was triturated with pet ether and 27.2 g of product filtered off. Crystallization from methanol afforded analytical material, mp 168°-72° C.

Workup

  1. temperaturewas refluxed overnight
  2. customAfter evaporation
  3. customthe residue was partitioned between dilute NaOH solution and CHCl3
  4. customAfter drying
  5. custom(Na2SO4) and evaporation of the CHCl3
  6. extractionextract
  7. customthe residue was triturated with pet ether and 27.2 g of product
  8. filtrationfiltered off
  9. customCrystallization from methanol afforded analytical material, mp 168°-72° C.

Sources & evidence

ORD record
ord-746a9249a5b34e639b989759080b3afd
Source dataset
uspto-grants-1981_06
Patent number
US04276296

Reaction notes

Loading…