Sodium hydride → HCID 54227746, compound

HRID 2225824Notes

Reaction equation

HRID 2225824 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:2].[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][N:21]1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]1=2>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:18][CH2:19][CH2:20][N:21]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]2=3)=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 19004329HCID 19004329, compound

Product 1

HCID 54227746HCID 54227746, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.376 g) in dimethylformamide (5 mL) was treated with 55% sodium hydride (0.085 g), stirred for 15 minutes and then 5-(3-bromopropyl)-5,6-dihydro-6-oxophenanthridine (0.613 g) in dimethylformamide (5 mL) was added. The mixture was stirred at room temperature for 22 hours and worked up as in Example 20. The residual oil was purified by HPLC (ethyl acetate-hexane; 7:13), and crystallization of the resulting solid from ethyl acetate-tetrahydrofuran gave 0.4 g of 4-[3-(5,6-dihydro-6-oxo-5-phenanthridinyl)propoxy]-alpha-oxobenzeneacetic acid ethyl ester, mp 95°-97° C. A second crop of the title compound (0.16 g, mp 95°-97° C.) was recovered from the mother liquor.

Workup

  1. stirringThe mixture was stirred at room temperature for 22 hours
  2. customThe residual oil was purified by HPLC (ethyl acetate-hexane; 7:13), and crystallization of the resulting solid from ethyl acetate-tetrahydrofuran

Sources & evidence

ORD record
ord-93bd254f80cd467795e116cdff252fca
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…