Carbon Dioxide → HCID 13478464, compound

HRID 436488Notes

Reaction equation

HRID 436488 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8][CH2:9][C:10]=2[CH:11]=1.[CH2:14]([Li])CCC.[C:19](=[O:21])=[O:20]>CCOCC.CCCCCC>[CH3:14][O:20][C:19]([CH:6]1[C:5]2[N:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:10]=2[CH2:9][CH2:8][C:7]1([CH3:13])[CH3:12])=[O:21]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 122782055,6,7,8-Tetrahydro-3,7,7-trimethylquinolineHCID 178418339Butyllithium

Product 1

HCID 13478464HCID 13478464, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

3,7,7-Trimethyl-5,6,7,8-tetrahydroquinoline (17.5 g., 0.1 m) was dissolved in dry ether (200 ml.) and treated with a solution of n-butyl lithium in hexane (15% solution, 56 ml.) under nitrogen. The reaction mixture was allowed to stand at room temperature for 30 minutes and then treated with CO2 gas until the intense red colour was discharged. The solvent was removed and the residual oily solid dissolved in water (20 ml.) then extracted with ether (3 × 50 ml.). The ethereal extracts were retained to recover unreacted starting material. The aqueous solution was evaporated to dryness, the residue treated with methanol previously saturated with dry HCl (100 ml.) and the solution allowed to stand at room temperature for 8 hours. The solvent was removed and the residual oil dissolved in water (50 ml.) and extracted with ether (3 × 50 ml.) and the extracts discarded. The aqueous solution was adjusted to pH 9.0 with sodium carbonate and extracted with ether (3 × 50 ml.). The combined extracts were dried and evaporated in vacuo to give the title compound as a pale yellow oil (1.8 g., 10 %) I.R. Spectrum νmax film 1748, 1570, 1460, 1160, 1030 cm-1. GLC : RT =3.1/2 min. (F11, 2% OV17, T = 150°).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residual oily solid dissolved in water (20 ml.)
  3. extractionthen extracted with ether (3 × 50 ml.)
  4. customto recover unreacted
  5. customThe aqueous solution was evaporated to dryness
  6. additionthe residue treated with methanol previously saturated with dry HCl (100 ml.)
  7. waitto stand at room temperature for 8 hours
  8. customThe solvent was removed
  9. dissolutionthe residual oil dissolved in water (50 ml.)
  10. extractionextracted with ether (3 × 50 ml.)
  11. extractionextracted with ether (3 × 50 ml.)
  12. customThe combined extracts were dried
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-dc4ac0b761c3468c998f6bb8c45c8453
Source dataset
uspto-grants-1977_02
Patent number
US04009169

Reaction notes

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