Hydrochloric Acid → HCID 15410463, compound

HRID 362380Notes

Reaction equation

HRID 362380 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:26]=1[C:27](Cl)=[O:28].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:26]=1[C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=3)=[O:7])=[CH:22][CH:23]=1)=[O:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 783922,6-Dichlorobenzoyl chlorideHCID 15410466HCID 15410466, compound

Product 1

HCID 15410463HCID 15410463, compoundYield 240.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 300 mg (0.5 mmol) of 5-(4-aminobenzoyl)-5,6-dihydrophenanthridine and 230 mg of (0.55 mmol) of 2,6-dichlorobenzoyl chloride in 1.2 ml of pyridine is heated (100° C.) for 3 hr and then stirred at room temperature for 6 days. To the mixture is added 10 mg of 4-(dimethylamino)pyridine and the mixture stirred for 22 days. To the mixture is added 6 ml of 2N HCl and the solid filtered and washed with 2N HCl, 1N NaOH, H2O to give 0.57 g of solid. The solid is chromatographed on thick layer silica gel plates with hexane ethyl-acetate (1:1) to give 110 mg of solid. Recrystallization from CH2Cl2 -diisopropyl ether to give 73 mg of white crystals, m.p. 230°-235° C.

Workup

  1. stirringthe mixture stirred for 22 days
  2. filtrationthe solid filtered
  3. washwashed with 2N HCl, 1N NaOH, H2O

Sources & evidence

ORD record
ord-348f85d4ee9042598252293f172f28f3
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

Loading…