Water → 6-(4-Amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one

HRID 271199Notes

Reaction equation

HRID 271199 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:21]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:18])[N:11]([CH3:19])[N:10]=1.C(N)CCC.O>CO>[NH2:21][C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([O:8][C:9]2[CH:14]=[C:13]([CH:15]([CH3:16])[CH3:17])[C:12](=[O:18])[N:11]([CH3:19])[N:10]=2)=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8007ButylamineHCID 598345522-[3,5-Dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-isoindole-1,3-dione

Product 1

HCID 598344456-(4-Amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-oneYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-isoindole-1,3-dione (66) (64 g, 139.6 mmol) in methanol (500 mL) was treated with butylamine (34.67 mL, 349 mmol). The mixture was heated to reflux for 1.5 h. At this time, the reaction was cooled to room temperature and treated dropwise with water (384 mL). The resulting solids were collected by filtration, washed with a 1:1 solution of methanol/water (180 mL) followed by water (250 mL) and dried under vacuum to afford 6-(4-amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one (67) (34.12 g, 74.4%) as an off-white solid; ES(+)-LRMS for C14H15Cl2N3O2 (M+H)+ at m/z=328. Exact Mass=327.0541; Molecular Weight=328.20.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with a 1:1 solution of methanol/water (180 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-fc6a493a301d45e983e58a6e1cc75eda
Source dataset
uspto-grants-2008_11
Patent number
US07452882B2

Reaction notes

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