6-Chloroquinoline → 6-Chloro-1,2,3,4-tetrahydroquinoline

HRID 2043113Notes

Reaction equation

HRID 2043113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2>O=[Pt]=O.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 1

HCID 691636-Chloroquinoline

Product 1

HCID 111828396-Chloro-1,2,3,4-tetrahydroquinolineYield 62.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A flask filled with a mixture of 6-chloroquinoline (12.0 g, 73.3 mmol), PtO2 (2.16 g, 13 mol %), and MeOH (500 mL, 6.15 M) was flushed with N2 and then equipped with a balloon filled with H2. The reaction was kept under H2 atmosphere and stirred for 4 h. The mixture was filtered through Celite and washed with CH2Cl2. Purification via silica gel chromatography using 50% CH2Cl2 in hexanes gave 6-chloro-1,2,3,4-tetrahydroquinoline (7.7 g, 62%). 1H NMR (400 MHz, DMSO-d6) δ 6.85-6.83 (m, 2H), 6.42-6.39 (m, 1H), 5.82 (s, 1H), 3.17-3.13 (m, 2H), 2.64 (t, J=6.3 Hz, 2H), 1.78-1.72 (m, 2H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=168.2; tR=1.57 min.

Workup

  1. customwas flushed with N2
  2. customequipped with a balloon
  3. additionfilled with H2
  4. filtrationThe mixture was filtered through Celite
  5. washwashed with CH2Cl2
  6. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-6f98c39ca3b34e60b94b9b937d66faa1
Source dataset
uspto-grants-2013_11
Patent number
US08586589B2

Reaction notes

Loading…