Acetic Acid → Methyl 6-Oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate

HRID 877411노트

반응식

HRID 877411 반응식
O=[C:2]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:3](OC)=[O:4].O.[NH2:14][NH2:15].CC(O)=O>CO.C1(C)C=CC=CC=1>[O:4]=[C:3]1[NH:15][N:14]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:2]1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 25775Dimethyl alpha-ketoglutarate

생성물 1

HCID 12081646Methyl 6-Oxo-1,4,5,6-tetrahydropyridazine-3-carboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

Dimethyl 2-oxoglutarate (1.5 g, 8.98 mmol) was dissolved in MeOH (62 mL). Hydrazine monohydrate (500 mg, 9.88 mmol) and AcOH (540 mg, 8.98 mmol) were added to the solution sequentially. The reaction mixture was warmed at 70° C. for 18 h. The solution was cooled and reduced to a residue which was subsequently redissolved in toluene and evaporated to afford an off-white solid. The solid was tritrated with hexanes and needed no further purification (1.2 g, 100%): 1H NMR (CDCl3, 600 MHz) δ 8.75 (s, 1H), 3.90 (s, 3H), 2.93 (t, 2H, J=8.5 Hz), 2.58 (t, 2H, J=8.5 Hz).

후처리

  1. temperatureThe solution was cooled
  2. customevaporated
  3. customto afford an off-white solid
  4. customno further purification (1.2 g, 100%)

출처 및 근거

ORD 기록
ord-49e4f47e46034af4a7d88308f3ea8212
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987312B2

반응 노트

불러오는 중…