Sodium Hydroxide → HCID 15293915, compound

HRID 2210580Notes

Reaction equation

HRID 2210580 reaction equation
[C:1]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]([C:25]2[N:35]=[CH:34][CH:33]=[CH:32][C:26]=2[C:27]([O:29]CC)=[O:28])[CH2:21][CH2:22][O:23][CH3:24])=[CH:15][CH:14]=1)([C:3]([O:5]C)=[O:4])=[O:2].[OH-].[Na+]>O1CCOCC1>[CH3:24][O:23][CH2:22][CH2:21][N:20]([C:25]1[N:35]=[CH:34][CH:33]=[CH:32][C:26]=1[C:27]([OH:29])=[O:28])[CH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:1]([C:3]([OH:5])=[O:4])=[O:2])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19378986HCID 19378986, compound

Product 1

HCID 15293915HCID 15293915, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 535 mg of ethyl 2-{N-[(2'-methoxalylbiphenyl-4-yl)methyl]-N-(2-methoxyethyl)amino}nicotinate [prepared as described in step (a) above] dissolved in 4.5 ml of dioxane and a 1N aqueous solution of sodium hydroxide were mixed, and the resulting mixture was stirred at 50° C. for 19 hours. At the end of this time, the dioxane was removed by distillation under reduced pressure, and 4.5 ml of 1N aqueous hydrochloric acid was added to the residual aqueous solution. The crystals thus precipitated were collected by filtration, to give 306 mg of the title compound, melting at 173° C. (with decomposition).

Workup

  1. customAt the end of this time, the dioxane was removed by distillation under reduced pressure, and 4.5 ml of 1N aqueous hydrochloric acid
  2. additionwas added to the residual aqueous solution
  3. customThe crystals thus precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-b2f9937d3d3e41dfb0ca34ce68f65cde
Source dataset
uspto-grants-1995_10
Patent number
US05459148

Reaction notes

Loading…