Chloroacetone → 1,2,3,4-Tetrahydro-8,9-dimethyl-3-(2-oxopropyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 851201Notes

Reaction equation

HRID 851201 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[C:9]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:15](=[O:17])[O:16][C:4]=2[CH:3]=1.Cl[CH2:19][C:20](=[O:22])[CH3:21].C(N(CC)CC)C>C(O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[C:9]3[CH2:14][CH2:13][N:12]([CH2:19][C:20](=[O:22])[CH3:21])[CH2:11][C:10]=3[C:15](=[O:17])[O:16][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 131369151,2,3,4-Tetrahydro-8,9-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one

Product 1

HCID 131369311,2,3,4-Tetrahydro-8,9-dimethyl-3-(2-oxopropyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-oneYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-8,9-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one (30 g, 0.13 mole), 1-chloro-2-propanone (23.6 g, 0.25 moles), and triethylamine (27.3 g, 0.27 moles) in 550 ml of absolute ethanol is stirred at reflux for 21 hours. The reaction mixture is evaporated, and the residue is partitioned between dichloromethane (700 ml) and water (500 ml). The two-phase mixture is made basic with conc. ammonium hydroxide, the layers are separated, and the aqueous phase is extracted with fresh dichloromethane. The combined organic layers are backwashed with water, dried over sodium sulfate, and evaporated. Recrystallization of the residue from absolute ethanol yielded the product (23.5 g), mp 136°-138° C.

Workup

  1. temperatureat reflux for 21 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue is partitioned between dichloromethane (700 ml) and water (500 ml)
  4. customthe layers are separated
  5. extractionthe aqueous phase is extracted with fresh dichloromethane
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customRecrystallization of the residue from absolute ethanol

Sources & evidence

ORD record
ord-66e1c10dfbfb46728d02b3c873cdcd15
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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