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

HRID 651225Notes

Reaction equation

HRID 651225 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 suspension of the 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. additionwas added
  2. additionIt was then poured
  3. customover crushed ice
  4. customthe solid obtained
  5. washwas washed thoroughly with cold water
  6. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-b096fcd348e54521b7f67f39d3372f59
Source dataset
uspto-grants-2001_08
Patent number
US06277990B1

Reaction notes

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