Sodium Hydroxide → HCID 18378701, compound

HRID 1767550Notes

Reaction equation

HRID 1767550 reaction equation
O.NN.[OH-].[Na+].[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=O)[CH2:14][N:15]1[C:23]2[C:18](=[N:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1>C(O)COCCO>[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][N:15]1[C:23]2[C:18](=[N:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[CH:17]=[CH:16]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 18758227HCID 18758227, compound

Product 1

HCID 18378701HCID 18378701, compound

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

140 μl (2.9 mmol) of hydrazine hydrate and 80 mg (2 mmol) of sodium hydroxide are added to a solution of 200 mg (0.6 mmol) of the compound obtained in Step B in 2 ml of diethylene glycol. After 24 hours' stirring at 160° C., the mixture is hydrolysed and then extracted with ethyl acetate. The organic phase is washed several times with water, dried over magnesium sulphate, concentrated and then purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 7:3) to yield the title compound in the form of a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed several times with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. custompurified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-68452850f2464fb695ce3858a38fd73f
Source dataset
uspto-grants-2007_06
Patent number
US07235550B2

Reaction notes

Loading…