Methylamine → 5,7-Dichloro-2-methylamino-8-hydroxyquinoline

HRID 1754093Notes

Reaction equation

HRID 1754093 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:14])[C:6]([Cl:13])=[CH:7][C:8]=2[Cl:12])[N:3]=1.[CH3:15][NH2:16]>C(O)C>[Cl:12][C:8]1[CH:7]=[C:6]([Cl:13])[C:5]([OH:14])=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([NH:16][CH3:15])=[N:3]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 7627422,5,7-trichloroquinolin-8-ol

Product 1

HCID 116659195,7-Dichloro-2-methylamino-8-hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,5,7-Trichloro-8-hydroxyquinoline 10 (200 mg, 0.805 mmol) and a solution of methylamine in ethanol (12 mL of a 33% solution) were heated in a sealed vessel at 90° C. for 26 h, and cooled. The precipitate was then isolated via filtration and washed with diethyl ether. This provided pure 5,7-dichloro-2-methylamino-8-hydroxyquinoline (PBT 1047) as a pale yellow solid (186 mg, 95%). 1H NMR (DMSO-d6, 400 MHz): δ 8.80 (br, 1 H), 7.98 (d, J=9.1, 1 H), 7.48 (br, 1 H), 7.25 (s, 1 H), 6.90 (d, J=9.1, 1H), 2.98 (d, J=4.8, 3 H); mass spectrum: m/z 243, 245 (M++1, 100 and 66%, respectively).

Workup

  1. temperaturecooled
  2. customThe precipitate was then isolated via filtration
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-9ef6fcd9ccaa478995fe70e54989cad1
Source dataset
uspto-grants-2015_10
Patent number
US09169211B2

Reaction notes

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