Ammonia → 3-Methyl-8-quinolinamine

HRID 513384

Reaction equation

HRID 513384 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2O.S([O-])([O-])=O.[NH4+:17].[NH4+].N>O>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH2:17]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25041Ammonium SulfiteHCID 43322813-Methylquinolin-8-ol2×

Product 1

HCID 157837943-Methyl-8-quinolinamineYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-methylquinolin-8-ol (Intermediate 30) (150 mg, 0.9 mmol) and ammonium sulphite (250 mg, 1.8 mmol) were added to aqueous ammonia (3 ml) and heated for 48 h. After cooling, water was added and the mixture was extracted with DCM. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound (130 mg, 86%).

Workup

  1. temperatureheated for 48 h
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-deb45c358e1b499eb3e02cc0c03b2144
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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