2-Oxoglutaric Acid → 2-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)acetic acid

HRID 1110024Notes

Reaction equation

HRID 1110024 reaction equation
N[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.O=[C:13]([CH2:17][CH2:18]C(O)=O)[C:14]([OH:16])=[O:15]>C(O)(=O)C.Cl.O>[C:17]1([CH2:13][C:14]([OH:16])=[O:15])[C:10]2=[C:11]3[C:6](=[CH:7][CH:8]=[CH:9]2)[CH2:5][CH2:4][CH2:3][N:2]3[CH:18]=1

Participants

6

Reactant 2

HCID 512-Oxoglutaric AcidHCID 64233141,2,3,4-Tetrahydroquinolin-1-amine

Product 1

HCID 100591342-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)acetic acidYield 42.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

17 g of 1-amino-1,2,3,4-tetrahydroquinoline (preparation see Example 1B) and 20 g of 2-ketoglutaric acid were heated under reflux at a temperature of 80° C. for 2 hours in a mixture of 160 ml of acetic acid and 11.4 ml of concentrated hydrochloric acid. To work up the reaction mixture the solid residue which remained was taken up in water and extracted with ethyl acetate. The organic phase was separated and extracted with 20% strength aqueous sodium hydroxide solution. The alkaline (pH=9) aqueous phase was separated and acidified to pH=4 by addition of aqueous 10% strength hydrochloric acid solution, and a precipitate formed. The solution was extracted with ethyl acetate. The organic phase was evaporated. 10.6 g of crude 5,6-dihydro- 4H-pyrrolo-[3,2,1-ij]quinoline-1-acetic acid were obtained as a solid residue.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was separated
  3. extractionextracted with 20% strength aqueous sodium hydroxide solution
  4. customThe alkaline (pH=9) aqueous phase was separated
  5. additionacidified to pH=4 by addition of aqueous 10% strength hydrochloric acid solution
  6. customa precipitate formed
  7. extractionThe solution was extracted with ethyl acetate
  8. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-3a09e64615584ab2ac0df9b3fbf85e7a
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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