Triethylamine → HCID 19068039, compound

HRID 1957551Notes

Reaction equation

HRID 1957551 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[C:11]([CH2:20][CH:21]=[CH2:22])[C:12]([OH:19])=[C:13]([CH2:16][CH:17]=[CH2:18])[CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:23].Cl.C([O:27][C:28](=[O:32])[CH2:29][NH:30][CH3:31])C.C(N(CC)CC)C.O.N>C(#N)C>[C:28]([CH2:29][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[C:11]([CH2:20][CH:21]=[CH2:22])[C:12]([OH:19])=[C:13]([CH2:16][CH:17]=[CH2:18])[CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:23])[CH3:31])([OH:32])=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 12896473Azane;hydrateHCID 19067881HCID 19067881, compound

Product 1

HCID 19068039HCID 19068039, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-Bromobutyl)-5,7-diallyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone (1.9 g) was dissolved in 50 ml of acetonitrile, then 2 g of N-methylglycine ethyl ester hydrochloride and 5 ml of triethylamine were added thereto, and stirred at 80° C. for 4 hours. The reaction mixture was extracted with ethyl acetate, the extract was washed with an aqueous solution saturated with sodium bicarbonate, next with water, then concentrated under reduced pressure. Thus obtained oily residual product was subjected to purification by means of a silica gel column chromatography, then dissolved in 10 ml of methanol and 10 ml of 1N-sodium hydroxide aqueous solution, and stirred at 70° C. for 1 hour. After the reaction mixture was cooled, the mixture was acidified by adding hydrochloric acid, further the acidified reaction mixture was made basic by adding 25% ammonia water. This reaction mixture was concentrated under reduced pressure to dryness, thus obtained solid residual product was subjected to extraction by means of Soxhlet's extractor with chloroform as the solvent. The chloroform extract was concentrated under reduced pressure to dryness, and recrystallized from acetone, there was obtained 1-[4-(N-carboxymethyl-N-methyl-amino)butyl ]-5,7-diallyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with an aqueous solution saturated with sodium bicarbonate, next with water
  3. concentrationconcentrated under reduced pressure
  4. customThus obtained oily residual product was subjected to purification by means of a silica gel column chromatography
  5. dissolutiondissolved in 10 ml of methanol
  6. stirring10 ml of 1N-sodium hydroxide aqueous solution, and stirred at 70° C. for 1 hour
  7. temperatureAfter the reaction mixture was cooled
  8. additionby adding hydrochloric acid
  9. customfurther the acidified reaction mixture
  10. concentrationThis reaction mixture was concentrated under reduced pressure to dryness, thus obtained solid residual product
  11. extractionwas subjected to extraction by means of Soxhlet's extractor with chloroform as the solvent
  12. extractionThe chloroform extract
  13. concentrationwas concentrated under reduced pressure to dryness
  14. customrecrystallized from acetone

Sources & evidence

ORD record
ord-de9ec42d4e6b4369abe7d3592bbf541e
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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