Azane;hydrate → HCID 19068023, compound

HRID 1957547Notes

Reaction equation

HRID 1957547 reaction equation
[CH2:1]([C:4]1[C:13]([OH:14])=[C:12]([CH2:15][CH:16]=[CH2:17])[CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:24])[N:9]2[CH2:18][C:19](OCC)=[O:20])[CH:2]=[CH2:3].O.[NH3:26]>CO>[C:19]([CH2:18][N:9]1[C:10]2[C:5](=[C:4]([CH2:1][CH:2]=[CH2:3])[C:13]([OH:14])=[C:12]([CH2:15][CH:16]=[CH2:17])[CH:11]=2)[CH2:6][CH2:7][C:8]1=[O:24])(=[O:20])[NH2:26]

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 19068021HCID 19068021, compound

Product 1

HCID 19068023HCID 19068023, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.65 Grams of 5,7-diallyl-1-(ethoxy-carbonylmethyl)-3,4-dihydro-6-hydroxy-2(1H)-quinolinone obtained in Example 57 was dissolved in 50 ml of methanol, then 20 ml of 25% ammonia water thereto, the reaction mixture was stirred for 24 hours. Then the reaction mixture was concentrated under reduced pressure. The concentrate was extracted with chloroform, washed with water, dried, then concentrated again under reduced pressure. Thus obtained crude crystals were subjected to purification by passing it through a silica gel column and by using methylene chloridemethanol (50:1) as the eluent, there was obtained 1.2 g (80%) of 1-(carbamoylmethyl)-5,7-diallyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone.

Workup

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. extractionThe concentrate was extracted with chloroform
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated again under reduced pressure
  6. customThus obtained crude crystals
  7. customwere subjected to purification

Sources & evidence

ORD record
ord-159cc6499bf14a779166553a5d164f30
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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