Hydrochloric Acid → N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide

HRID 1016484Notes

Reaction equation

HRID 1016484 reaction equation
Cl.[NH2:2][C:3]1[CH:16]=[CH:15][C:14]2[NH:13][C:12](=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21]>CN(C=O)C.N1C=CC=CC=1>[O:17]=[C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[CH:4]=[C:3]([NH:2][C:20](=[O:21])[CH2:19][Cl:18])[CH:16]=[CH:15][C:14]=2[NH:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 2706686(5h)-Phenanthridinone, 2-amino-

Product 1

HCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamideYield 828.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To a supension of HCl salt of 2-amino-6(5H)-phenanthridinone (100 mg, 0.04 mmol) in DMF (5 mL), pyridine (0.5 mL) was added, followed by the addition of chloroacetyl chloride (0.2 mL, 0.002 mol) at 0° C. The reaction mixture was stirred at room temperature for 1 to 2 hrs. It was then poured over crushed ice, and the solid obtained was washed thoroughly with cold water. The solid was then dried under vacuum to give N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-choroacetamide (95 mg, 84%).

Workup

  1. additionIt was then poured
  2. customover crushed ice
  3. customthe solid obtained
  4. washwas washed thoroughly with cold water
  5. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-7e6e15e4db544a1b907e1448811c5aa0
Source dataset
uspto-grants-2002_11
Patent number
US06476048B1

Reaction notes

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