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

HRID 651224Notes

Reaction equation

HRID 651224 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 2706682-Aminophenanthridin-6-olHCID 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-b5ddc2928a1f4b2ab554273348e5483d
Source dataset
uspto-grants-2001_08
Patent number
US06277990B1

Reaction notes

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