Chloroacetyl chloride → N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide

HRID 2086008Notes

Reaction equation

HRID 2086008 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11](=[O:16])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1.[Cl:17][CH2:18][C:19](Cl)=[O:20].[OH-].[Na+]>C1OCCOC1>[Cl:17][CH2:18][C:19]([NH:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11](=[O:16])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1)=[O:20]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 2706686(5h)-Phenanthridinone, 2-amino-

Product 1

HCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamideYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Prepared from 2-amino-6(5H)-phenanthridinone 3 and chloroacetyl chloride according to General Procedure A. P-dioxane was used as solvent and 1.1 equivalent of sodium hydroxide as base. A white precipitation was formed after stirring the mixture for 2 ours. Purification of the precipitation by crystallization in dioxane gave a white solid (53% yield), mp 300-303° C. 1H-NMR (400 MHz, DMSO-d6), 11.71 (s, 1H), 10.45 (s, 1H), 8.63 (s, 1H), 8.33 (d, J=7.9 Hz, 1H), 8.27 (d, J=8.2 Hz, 1H), 7.89 (d, J=7.6 Hz, 1H), 7.46 (m, 2H), 7.34 (d, J=8.8 Hz, 1H), 4.30 (s, 2H). Anal. (C15H11ClN2O2), C H N.

Workup

  1. customA white precipitation
  2. customwas formed
  3. customPurification of the precipitation
  4. customby crystallization in dioxane

Sources & evidence

ORD record
ord-4430ff67d1f94e2ba260e62d3cac78ac
Source dataset
uspto-grants-2004_04
Patent number
US06723733B2

Reaction notes

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