Methylamine → 2-Methylamino-N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-acetamide

HRID 1618117Notes

Reaction equation

HRID 1618117 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]2[NH:16][C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=1)=[O:4].[CH3:21][NH2:22]>CN(C)C=O.C(O)C>[CH3:21][NH:22][CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]2[NH:16][C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=1)=[O:4]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide

Product 1

HCID 668198452-Methylamino-N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-acetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 2-chloro-N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-acetamide (XXIV, Lg=Cl) (150 mg, 0.52 mmol) in dimethylformamide (1.4 mL), a 33% solution of methylamine in ethanol was added (9 mL, 72 mmol). The reaction mixture was stirred at room temperature for 3 hours. The ethanol was then evaporated under reduced pressure and the mixture was diluted with diethyl ether and filtered. A light-yellow solid was then collected, washed with diethyl ether then with cold water and dried. 2-Methylamino-N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-acetamide was obtained in moderate yield (100 mg, 68%).

Workup

  1. customThe ethanol was then evaporated under reduced pressure
  2. additionthe mixture was diluted with diethyl ether
  3. filtrationfiltered
  4. customA light-yellow solid was then collected
  5. washwashed with diethyl ether
  6. dry with materialwith cold water and dried

Sources & evidence

ORD record
ord-879423239b0f43deb821b674e60b6ac2
Source dataset
uspto-grants-2014_07
Patent number
US08765972B2

Reaction notes

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