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

HRID 877411ノート

反応式

HRID 877411 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-49e4f47e46034af4a7d88308f3ea8212
出典データセット
uspto-grants-2015_03
特許番号
US08987312B2

反応ノート

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