Ethyl bromoacetate → Pyridazineacetic acid, 1-, (6H), 3-chloro-6-oxo-, ethyl ester

HRID 572693ノート

反応式

HRID 572693 の反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:7]=1

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178516069HCID 178516069、化合物

生成物 1

HCID 144466Pyridazineacetic acid, 1-, (6H), 3-chloro-6-oxo-, ethyl ester収率 60.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-chloropyridazin-3-ol (0.5 g, 3.83 mmol, WO2011015629) in DMF (5 mL) was added potassium carbonate (1.059 g, 7.66 mmol, Rankem) followed by ethyl 2-bromoacetate (0.960 g, 5.75 mmol, Spectrochem). The reaction mixture was stirred at RT for 5 h. The reaction mixture was quenched with water (2 mL) and the product was extracted with EtOAc (3×20 mL). Combined organic layers were washed successively with water (20 mL) and brine (20 mL). The organic layer was dried over sodium sulphate and evaporated under vacuum to afford ethyl 2-(3-chloro-6-oxopyridazin-1(6H)-yl)acetate 0.5 g (60.3%) as pale yellow solids. 1H NMR (400 MHz, CDCl3): δ 7.266-7.236 (d, J=12 Hz, 1H), 6.965-6.945 (d, J=7.6 Hz, 1H) 4.819 (s, 2H) 4.273-4.230 (m, 2H) 1.309-1.279 (m, 3H); MS m/z=217.2 (M+H)+.

後処理

  1. customThe reaction mixture was quenched with water (2 mL)
  2. extractionthe product was extracted with EtOAc (3×20 mL)
  3. washCombined organic layers were washed successively with water (20 mL) and brine (20 mL)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated under vacuum

出典と根拠

ORDレコード
ord-331b298b90dc406bac6f9ebccff84bbc
出典データセット
uspto-grants-2015_05
特許番号
US09029409B2

反応ノート

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