HCID 13603776, compound → HCID 13519806, compound

HRID 1380656Notes

Reaction equation

HRID 1380656 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH2:12][CH2:13][C:14]([OH:16])=O)[CH:6]=[CH:7][CH:8]=2)[NH:3]1>C(OC(=O)C)(=O)C>[CH2:10]1[C:9]2=[CH:8][CH:7]=[CH:6][C:5]3=[C:4]2[N:3]([C:14](=[O:16])[CH2:13][CH2:12]3)[C:2](=[O:1])[CH2:11]1

Participants

3

Reactant 1

HCID 13603776HCID 13603776, compound

Product 1

HCID 13519806HCID 13519806, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

1,2,3,4-Tetrahydro-2-oxo-8-quinolinepropanoic acid (2.1 g, 0.0096 mole) is dissolved in acetic anhydride (10 ml) and the solution is heated to 100° C. for one hour. Excess acetic anhydride is removed at reduced pressure and the residual anhydride is removed by addition of toluene and repeated concentration. The solid is recrystallized from ethyl acetate to yield pure 1,2,6,7-tetrahydro-3H,5H-benzo[ij]-quinolizine-3,5-dione, mp 136°-140° C.

Workup

  1. customExcess acetic anhydride is removed at reduced pressure
  2. customthe residual anhydride is removed by addition of toluene
  3. concentrationconcentration
  4. customThe solid is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-dea381f0966749ccab4d86e2a94546a0
Source dataset
uspto-grants-1986_04
Patent number
US04582909

Reaction notes

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