Hydrochloric Acid → 5-(2,6-difluoro-phenoxy)-2H-pyridazin-3-one

HRID 2381299Notes

Reaction equation

HRID 2381299 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:3]=1[O:4][C:5]1[CH:10]=[N:9][N:8](C2CCCCO2)[C:7](=[O:17])[CH:6]=1.Cl.O>CO>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:3]=1[O:4][C:5]1[CH:10]=[N:9][NH:8][C:7](=[O:17])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 668753985-(2,6-difluoro-phenoxy)-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one

Product 1

HCID 579192725-(2,6-difluoro-phenoxy)-2H-pyridazin-3-oneYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 5-(2,6-difluoro-phenoxy)-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (92.3 mg, 0.30 mmol) in methanol (0.6 mL, 0.5M) was treated with a 6N aqueous hydrochloric acid solution (0.25 L, 1.2M). The reaction was heated at 110° C. for 1 h and then stood at 25° C. overnight. At this point, the reaction was charged with water (10 mL). The solids were crushed, filtered, rinsed, and dried in vacuo to afford 5-(2,6-difluoro-phenoxy)-2H-pyridazin-3-one (45.7 mg, 68%) as an off-white solid; 1H-NMR (400 MHz, DMSO-d6) δ ppm 5.91 (s, 1H), 7.25-7.43 (m, 2H), 7.43-7.57 (m, 1H), 8.11 (d, J=2.6 Hz, 1H), 13.10 (brs, 1H).

Workup

  1. customThe solids were crushed
  2. filtrationfiltered
  3. washrinsed
  4. customdried in vacuo

Sources & evidence

ORD record
ord-16b22a2b46184d4cb97adceea7ae03e1
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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