Triethylamine → Quinoline

HRID 650895Notes

Reaction equation

HRID 650895 reaction equation
Cl.NC[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[C:7](O)[CH:8]=[CH:9][CH:10]=2)[N:5]=1.C(N(CC)CC)C>C(#N)C>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][CH:4]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 21710115HCID 21710115, compound

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-aminomethyl-8-hydroxyquinoline hydrochloride (1.05 g, 5 mmol) N-succinimidyl S-tetrahydropyranylmercaptoacetate (1.37 g, 5 mmol), and triethylamine (0.51 g, 5 mmol) in acetonitrile (15 mL) was heated under reflux for 2 hours. The reaction mixture was poured onto water and extracted with methylene chloride (3×20 mL). The combined organic layers were washed with water and dried (MgSO4) to give the ligand of Formula 17 as an orange gum which was sufficiently pure for complexation purposes. 1H-NMR (CDCl3) δ8.42 (broad, 1H), 8.20 (d, 1H), 7.41 (d, 1H), 7.35 (m, 2H), 7.18 (d, 1H), 4.95 (dd, 1H), 4.82(dd, 1H), 4.73 (dd, 1H), 4.00 (m, 1H), 3.78 (m, 1H), 3.57 (d, 1H), 3.35 (d, 1H), 2.10-1.55 (m, 6H); 13C-NMR (CDCl3) δ169.6, 154.1, 152.1, 137.0, 136.9, 127.5, 127.4, 120.2, 117.8, 110.9, 83.7, 65.5, 44.7, 35.2, 30.8, 25.0, 21.6.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. additionThe reaction mixture was poured onto water
  4. extractionextracted with methylene chloride (3×20 mL)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-911f2332aa014bc5a79f26ffb26d4af1
Source dataset
uspto-grants-2001_08
Patent number
US06277841B1

Reaction notes

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