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

HRID 2045969Notes

Reaction equation

HRID 2045969 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 150 mg of 2-chloro-N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-acetamide (XV) (0.52 mmol) in N,N-dimethylformamide (1.4 mL), 9 mL of a 33% solution of methylamine in ethanol were added (mM). 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 ether then with cold water and dried. The title compound was obtained in moderate yield (100 mg, 68%).

Workup

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

Sources & evidence

ORD record
ord-573228e3c0f643a78dd80cede0e2d56d
Source dataset
uspto-grants-2013_11
Patent number
US08592416B2

Reaction notes

Loading…