Sodium Hydroxide → HCID 14963380, compound

HRID 2399260Notes

Reaction equation

HRID 2399260 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11](=O)[NH:12][N:13]=1.P(Cl)(Cl)([Cl:24])=O.[OH-].[Na+]>O>[Cl:24][C:11]1[N:12]=[N:13][C:8]([CH2:7][CH2:6][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 14963379HCID 14963379, compound

Product 1

HCID 14963380HCID 14963380, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-(3,4,5-Trimethoxyphenethyl)pyridazin-3(2H)-one (2.80 g; 9.65 mmol) and phosphorus oxychloride (70 ml) was heated at 100° for 1 h, cooled to room temperature and hydrolysed by careful, gradual addition to water over 3 h, so that the temperature did not exceed 30°. The mixture was then basified to pH12 by the addition of sodium hydroxide solution (10N, 700 ml) and then left at 4° overnight. The precipitate was filtered at the pump, washed well with water to remove inorganic salts and the residue on the sinter taken up in dichloromethane. After drying (sodium sulphate), removal of the solvent gave a light-brown solid (2.84 g) which was purified by `flash` chromatography on silica, with 10% of ethyl acetate/dichloromethane as the eluent. Appropriate fractions were combined to give a white solid (2.16 g), m.p. 105°-106°.

Workup

  1. temperaturewas heated at 100° for 1 h
  2. customdid not exceed 30°
  3. filtrationThe precipitate was filtered at the pump
  4. washwashed well with water
  5. customto remove inorganic salts
  6. customAfter drying
  7. custom(sodium sulphate), removal of the solvent

Sources & evidence

ORD record
ord-2847ac89f68d454e9c8964e00fbeb446
Source dataset
uspto-grants-1995_09
Patent number
US05447956

Reaction notes

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