Sodium Hydroxide → HCID 178516200, compound

HRID 2424282Notes

Reaction equation

HRID 2424282 reaction equation
[CH2:1]1[CH:3]2[CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[C:9]([O:11][C:12]4[N:13]=[N:14][C:15]([Cl:19])=[CH:16][C:17]=4[OH:18])[C:10]=3[CH:2]12.[OH-].[Na+]>CS(C)=O>[CH2:1]1[CH:3]2[CH2:2][C:10]3[C:9]([O:11][C:12]4[N:13]=[N:14][C:15]([Cl:19])=[CH:16][C:17]=4[OH:18])=[CH:8][CH:7]=[CH:6][C:5]=3[CH:4]12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178516199HCID 178516199, compound

Product 1

HCID 178516200HCID 178516200, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In dimethylsulfoxide (3 mL) was dissolved 32.6 mg (0.111 mmol) of 3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-yloxy)-4,6-dichloropyridazine obtained in Example 14 (8), and 0.1 mL (0.2 mmol) of 2 mol/L aqueous sodium hydroxide solution was added to the solution and the resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into ice-cold 1 mol/L aqueous sodium hydroxide solution, and washed with ethyl acetate. The aqueous layer was separated, conc. hydrochloric acid was added thereto to adjust pH to 4 in an ice bath, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, dried over sodium sulfate. The solvent was distilled off and the obtained residue was purified by preparative thin-layer chromatography (available from Merck Co., 1.05744, 1 plate was used, developed by chloroform:methanol=10:1) to obtain 13.4 mg (0.0487 mmol, Yield: 43.9%) of 3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-yloxy)-6-chloro-4-pyridazinol (Compound No. 516).

Workup

  1. additionwas added to the solution
  2. washwashed with ethyl acetate
  3. customThe aqueous layer was separated
  4. additionconc. hydrochloric acid was added
  5. extractionextracted with ethyl acetate
  6. washwashed successively with water and brine
  7. dry with materialdried over sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe obtained residue was purified by preparative thin-layer chromatography (available from Merck Co., 1.05744, 1 plate was used, developed by chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-8f1b4176e16d467080f1f3a8ca909434
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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