Quinoline → HCID 18780613, compound

HRID 1421264Notes

Reaction equation

HRID 1421264 reaction equation
[CH2:1]([C:3]1[C:12]2[N:13]3[C:8]([CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)=[C:7](C(O)=O)[C:6](C(O)=O)=[C:5]3[C:4]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH3:2].N1C2C(=CC=CC=2)C=CC=1>[Cu]>[CH2:1]([C:3]1[C:12]2[N:13]3[C:8](=[CH:7][CH:6]=[C:5]3[C:4]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[CH3:2]

Participants

4

Reactant 2

HCID 7047QuinolineHCID 18706924HCID 18706924, compound

Product 1

HCID 18780613HCID 18780613, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
170 °C

Procedure

A mixture of 4-ethyl-6-methoxy-3-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid (1.75 g, 4.45 mmol), copper powder (0.4 g), and 90 ml of freshly purified quinoline was heated to 170° C. for eight hours in a nitrogen atmosphere. The copper catalyst was filtered off and the filtrate acidified with 6M hydrochloric acid and extracted with ether. The washed and dried (magnesium sulfate) extract was evaporated and the residue triturated with petroleum ether (40-60). The precipitate was filtered off and dried to afford 1.05 g (77%) of the title compound. M.p. 109-11° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.38 (t, 3H), 3.18 (q, 2H), 3.85 (s, 3H), 4.02 (s, 3H), 7.12 (d, 1H), 7.14 (d, 2H), 7.60 (d, 1H), 7.70-7.80 (m, 4H). (Compound 3).

Workup

  1. filtrationThe copper catalyst was filtered off
  2. extractionextracted with ether
  3. washThe washed
  4. dry with materialdried (magnesium sulfate)
  5. extractionextract
  6. customwas evaporated
  7. customthe residue triturated with petroleum ether (40-60)
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-a5b5ccb135304b8d8cd1ed27612881bf
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

Loading…