تفاعل #2286328

ord-225d52abbda24d32ab600355c934b899

معادلة التفاعل

CC(C)c1cc(Oc2c(Cl)cc(N3C(=O)c4ccccc4C3=O)cc2Cl)nn(C)c1=O
2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-isoindole-1,3-dione
CC(C)c1cc(Oc2c(Cl)cc(N3C(=O)c4ccccc4C3=O)cc2Cl)nn(C)c1=O
2-[3,5-Dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-isoindole-1,3-dione
CCCCN
butylamine
O
water
CC(C)c1cc(Oc2c(Cl)cc(N)cc2Cl)nn(C)c1=O
6-(4-amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one
المردود 74.5%
CC(C)c1cc(Oc2c(Cl)cc(N)cc2Cl)nn(C)c1=O
6-(4-Amino-2,6-dichlorophenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one
المردود 74.5%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe mixture was heated
  2. 2
    درجة الحرارةto reflux for 1.5 h
  3. 3
    ترشيحThe resulting solids were collected by filtration
  4. 4
    غسيلwashed with a 1:1 solution of methanol/water (180 mL)
  5. 5
    أخرىdried under vacuum

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: USRE046024E1uspto-grants-2016_06