Methylamine → HCID 70096011, compound

HRID 868987Notes

Reaction equation

HRID 868987 reaction equation
Cl[C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH3:16][NH2:17]>C(O)C>[CH3:16][NH:17][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15681445HCID 15681445, compound

Product 1

HCID 70096011HCID 70096011, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-chloro-8-methyl-5-nitroquinoline (420 mg, 1.9 mmol) in methanamine as a solution in ethyl alcohol (30 mL) was heated to 80° C. and stirred for 1 h. After concentration under reduced pressure, the reaction mixture was extracted with DCM (50 mL). The organic layer was washed with water (20 mL×2), dried over Na2SO4, and concentrated under reduced pressure to give 410 mg of N,8-dimethyl-5-nitroquinolin-6-amine as a yellow solid. MS (ESI): m/z 218 [M+H]+.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. extractionthe reaction mixture was extracted with DCM (50 mL)
  3. washThe organic layer was washed with water (20 mL×2)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-885e935a8d834104880de1fed459d7a4
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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