Hydrochloric Acid → HCID 19067980, compound

HRID 1957553Notes

Reaction equation

HRID 1957553 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH2:25][CH:26]=[CH2:27])[C:11]([O:18]C3CCCCO3)=[C:12]([CH2:15][CH:16]=[CH2:17])[CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:28])#[N:2].Cl>CO>[C:1]([CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH2:25][CH:26]=[CH2:27])[C:11]([OH:18])=[C:12]([CH2:15][CH:16]=[CH2:17])[CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:28])#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19067966HCID 19067966, compound

Product 1

HCID 19067980HCID 19067980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(2-Cyanoethyl)-5,7-diallyl-3,4-dihydro-6-(2-tetrahydropyranyloxy)-2(1H)-quinolinone (1 g) obtained in Example 95 was dissolved in 50 ml of methanol, then 6N-hydrochloric acid was added thereto and stirred at 60° C. for 30 minutes so as to remove the tetrahydropyranyl group, and concentrated under reduced pressure to dryness. Thus obtained residual product was subjected to purification by means of a silica gel column chromatography, then recrystallized from ethyl acetate-n-hexane, there was obtained 1-(2-cyanoethyl)-5,7-diallyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone.

Workup

  1. customto remove the tetrahydropyranyl group
  2. concentrationconcentrated under reduced pressure to dryness
  3. customThus obtained residual product was subjected to purification by means of a silica gel column chromatography
  4. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-b160a7bbcd9d444aae36328bbc342254
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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