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

HRID 1016482Notes

Reaction equation

HRID 1016482 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.C(=O)(O)[O-].[Na+].[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(OCC)(=O)C>[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:25](=[O:26])[CH2:24][Cl:23])[CH:16]=[CH:15][C:14]=2[NH:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 2706686(5h)-Phenanthridinone, 2-amino-HCID 516892Sodium Bicarbonate

Product 1

HCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamideYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of HCl salt of 2-amino-6(5H)-phenanthridinone (3.4 g, 0.014 mol) in ethyl acetate (200 mL) was added saturated solution of sodium bicarbonate (200 mL), followed by addition of chloroacetyl chloride (5.6 mL, 0.07 mol). The reaction mixture was stirred at room temperature for 2 days. The solid that separated out was filtered and washed thoroughly with cold water. It was then dried under vacuum to give N-(6-oxo-5, 6-dihydro-phenanthridin-2-yl)-chloroacetamide (3.35 gm, 85%).

Workup

  1. customThe solid that separated out
  2. filtrationwas filtered
  3. washwashed thoroughly with cold water
  4. customIt was then dried under vacuum

Sources & evidence

ORD record
ord-5e651c9c616c43bb8d0f7f2cbff76fa8
Source dataset
uspto-grants-2002_11
Patent number
US06476048B1

Reaction notes

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