methyl quinoline-3-carboxylate → HCID 11106176, compound

HRID 720730Notes

Reaction equation

HRID 720730 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13][CH3:14])=[O:12])[CH:2]=1>[Pt](=O)=O>[CH3:14][O:13][C:11]([C:3]1[CH:2]=[N:1][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1)=[O:12]

Participants

3

Reactant 1

HCID 257955methyl quinoline-3-carboxylate

Product 1

HCID 11106176HCID 11106176, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Conditions

Temperature
60 °C

Procedure

Representative procedure for small scale hydrogenation reactions. To a 2 or 3-neck, 100 ml round bottom flask containing a stir bar was added methyl quinoline-3-carboxylate (170 mg, 0.908 mol) and platinum (IV) oxide (10.3 mg, 5 mol %). The flask was equipped with two outlets sealed with rubber septa and containing Teflon stopcocks. Trifluoroacetic acid (3.0 mL), which was purged with argon gas to remove oxygen, was added via a plastic syringe into the reaction flask under an atmosphere of nitrogen. The stirred reaction mixture was flushed and the flask filled with hydrogen gas via a needle from a balloon through one of the septa-sealed outlets. The Teflon stopcocks were closed and the reaction mixture was warmed to 60° C. and stirred for 5 hours. The progress of the reaction was monitored by GC and TLC. The reaction mixture was cooled to room temperature and aqueous saturated sodium bicarbonate solution was added until the mixture was neutral. The mixture was then extracted with CH2Cl2 (3×30 mL), dried (MgSO4), and the solvent was removed in vacuo. The crude material thus obtained was separated by flash chromatography (silica gel, 10% EtOAc in hexanes). The title compound was obtained as a yellowish liquid (121 mg, 70%) which displayed: 1H NMR (CDCl3, 300 MHz): δ 1.80–2.00 (m, 4H), 2.79–2.85 (m, 2H), 2.90–3.00 (m, 2H), 3.91 (s, 3H), 7.95 (s, 1H), 8.93 (s, 1H); 13C NMR (CDCl3): δ 22.8, 23.1, 28.9, 30.0, 33.1, 52.5, 123.7, 132.5, 138.0, 148.2, 162.6, 166.5; MS m/z: 192 (M+H+). 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid methyl ester also was isolated (19 mg, 11%).

Workup

  1. additionTo a 2 or 3-neck, 100 ml round bottom flask containing a stir bar
  2. customThe flask was equipped with two outlets
  3. customsealed with rubber septa
  4. customTrifluoroacetic acid (3.0 mL), which was purged with argon gas
  5. customto remove oxygen
  6. additionwas added via a plastic syringe into the reaction flask under an atmosphere of nitrogen
  7. customThe stirred reaction mixture
  8. customwas flushed
  9. additionthe flask filled with hydrogen gas via a needle from a balloon through one of the septa-sealed outlets
  10. customThe Teflon stopcocks were closed
  11. temperatureThe reaction mixture was cooled to room temperature
  12. additionaqueous saturated sodium bicarbonate solution was added until the mixture
  13. extractionThe mixture was then extracted with CH2Cl2 (3×30 mL)
  14. dry with materialdried (MgSO4)
  15. customthe solvent was removed in vacuo
  16. customThe crude material thus obtained
  17. customwas separated by flash chromatography (silica gel, 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-35eae9f3d4fa4e10a6d71610ba89998e
Source dataset
uspto-grants-2006_11
Patent number
US07135570B2

Reaction notes

Loading…