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

HRID 2199146노트

반응식

HRID 2199146 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-225d52abbda24d32ab600355c934b899
출처 데이터셋
uspto-grants-2016_06
특허 번호
USRE046024E1

반응 노트

불러오는 중…