Ammonium Hydroxide → HCID 6404653, compound

HRID 1833841Notes

Reaction equation

HRID 1833841 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8](=O)[NH:9][N:10]=1.P(Cl)(Cl)([Cl:18])=O.[OH-].[NH4+]>CC(C)=O.O>[Cl:18][C:8]1[N:9]=[N:10][C:5]([CH2:4][C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=2[CH3:1])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 1485958HCID 1485958, compound

Product 1

HCID 6404653HCID 6404653, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

2,3-Dihydro-6-(2-methylbenzyl)pyridaz-3-one (prepared as described above; 36 g.) and phosphorus oxychloride (120 ml.) were heated together on a steam bath to 90° C. The dark red solution thus obtained was immediately cooled to 10°-15° C., diluted with acetone (125 ml.) and added to a stirred solution of acetone and aqueous ammonium hydroxide solution (s.g. 0.880) (1:1; 1000 ml.) maintained at a temperature of from 0° to 20° C. by strong cooling. The mixture was then diluted with water (1000 ml.). A light brown coloured solid was precipitated, filtered off, dried and dissolved in toluene (200 ml.). The toluene solution was filtered and the filtrate evaporated to dryness to give 3-chloro-6-(2-methylbenzyl)pyridazine (34 g.) in the form of an off-white coloured solid, m.p. 73.5° C.

Workup

  1. customThe dark red solution thus obtained
  2. temperaturewas immediately cooled to 10°-15° C.
  3. temperaturemaintained at a temperature of from 0° to 20° C. by strong cooling
  4. customA light brown coloured solid was precipitated
  5. filtrationfiltered off
  6. customdried
  7. dissolutiondissolved in toluene (200 ml.)
  8. filtrationThe toluene solution was filtered
  9. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-7447a6ac62d746909f4f3f4b10963948
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Reaction notes

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