7-Amino-2-methyl-1,2,3,4-tetrahydroquinoline → 2-Methylquinolin-7-amine

HRID 494190Notes

Reaction equation

HRID 494190 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH3:12])[NH:9]2)=[CH:4][CH:3]=1>C1(C)C(C)=CC=CC=1.[Pd]>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 685184487-Amino-2-methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 4596552-Methylquinolin-7-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 7-amino-2-methyl-1,2,3,4-tetrahydroquinoline (D65) (86 mg) and wet 10% palladium/charcoal (25 mg) in xylene (20 ml) was heated at reflux for 3.5 h. After cooling to room temperature the catalyst was removed via filtration and washed with further xylene. Evaporation of the combined filtrate and washings gave the title compound as a crude off-white solid (87 mg) which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.87 (d, 1H), 7.56 (d, 1H), 7.14 (d, 1H), 7.03 (d, 1H), 6.91 (dd, 1H), 4.02 (br, 2H), 2.67 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 h
  3. customwas removed via filtration
  4. washwashed with further xylene
  5. customEvaporation of the combined filtrate and washings

Sources & evidence

ORD record
ord-5d6e37a89b3c45379690756bddf6c78f
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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