Sodium Hydroxide → HCID 59427295, compound

HRID 1042801Notes

Reaction equation

HRID 1042801 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:15][CH3:16])[C:11](=O)[NH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:19])=O.CCN(C(C)C)C(C)C.[OH-].[Na+]>>[Cl:19][C:11]1[N:12]=[N:13][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:9][C:10]=1[CH2:15][CH3:16]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 67017177HCID 67017177, compound

Product 1

HCID 59427295HCID 59427295, compound

Conditions

Temperature
110 °C

Procedure

A RBF was charged with 6-(3-chlorophenyl)-4-ethylpyridazin-3(2H)-one (1.50 g, 6.4 mmol) and phosphorus oxychloride (6.0 ml, 64 mmol). Hunig's base (1.2 ml, 7.0 mmol) was added to the mixture dropwise (slightly exothermic). The flask was fitted with a reflux condenser and a nitrogen inlet and the mixture was heated at 110° C. for 3 h. Upon cooling the reaction mixture was poured onto ice. 6N NaOH was added dropwise until pH 9 while keeping the mixture cold by gradual addition of ice. The solids were filtered, washed with water and dried to provide 3-chloro-6-(3-chlorophenyl)-4-ethylpyridazine as a peach colored solid. MS m/z=253 [M]+. Calc'd for C12H10Cl2N2: 253.13.

Workup

  1. customThe flask was fitted with a reflux condenser and a nitrogen inlet
  2. temperatureUpon cooling the reaction mixture
  3. additionwas poured onto ice
  4. additioncold by gradual addition of ice
  5. filtrationThe solids were filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-ea51b42e36314060965787a60dfedd38
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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