Phosphorus oxychloride → 3-Chloro-6-cyclopropylpyridazine

HRID 1046064Notes

Reaction equation

HRID 1046064 reaction equation
[CH:1]1([C:4]2[N:9]=[N:8][C:7](O)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:7]1[N:8]=[N:9][C:4]([CH:1]2[CH2:3][CH2:2]2)=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515828HCID 178515828, compound

Product 1

HCID 523761673-Chloro-6-cyclopropylpyridazineYield 89%

Procedure

A mixture of 6-cyclopropylpyridazin-3-ol (182 mg, 1.3 mmol) in POCl3 (15 mL) was refluxed for 1 hour, and concentrated. The residue was treated with ethyl acetate (60 mL) and sat. NaHCO3 aqueous solution (10 mL) at 0° C. The organic layer was dried over Na2SO4 and concentrated to afford 3-chloro-6-cyclopropylpyridazine (185 mg, 89%). 1H NMR (400 MHz, CD3OD): δ1.11 (m, 2H), 1.20 (m, 2H), 2.25 (m, 1H), 7.52 (d, 1H), 7.67 (d, 1H).

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationconcentrated
  3. additionThe residue was treated with ethyl acetate (60 mL) and sat. NaHCO3 aqueous solution (10 mL) at 0° C
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f74fb5f10b2a4b78bf8376bdd2db14ac
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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