Dimethylformamide → Ethyl 8-Azido-4-Oxo-4H-Quinolizine-3-Carboxylate

HRID 48910

反応式

HRID 48910 の反応式
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2=[O:17].[N-:18]=[N+:19]=[N-:20].[Na+].CN(C=O)C>O>[N:18]([C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2=[O:17])=[N+:19]=[N-:20]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 3314858Ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate

生成物 1

HCID 20634157Ethyl 8-Azido-4-Oxo-4H-Quinolizine-3-Carboxylate収率 85%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

An oven-dried 25 ml round-bottom flask was purged with argon and charged with ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate (2) (250 mg, 1 mmol), NaN3 (300 mg, 4.6 mmol), and 5 ml DMF. The reaction mixture was stirred at 40° C. for 1 h, cooled to room temperature, and poured into 100 ml water. The aqueous layer was extracted three times with 100 ml chloroform, and the combined organic layers were washed three times with 100 ml water. The organic solvent was evaporated and the crude product was purified by flash chromatography (ethyl acetate) to give a deep red crystalline solid (218 mg, 85%). M.p. 145-150° C. 1H NMR (δ, CDCl3): 1.42 (t, J=7 Hz, 3H), 4.41 (q, J=7 Hz, 2H), 6.53 (d, J=8 Hz, 1H), 6.84 (dd, J=2 Hz, J=7 Hz, 1H), 7.08 (d, J=2 Hz, 1H), 8.37 (d, J=8 Hz, 1H), 9.36 (d, J=7 Hz, 1H). MS: m/z 258.0751; required for C12H10N4O3: 258.0753.

後処理

  1. customAn oven-dried 25 ml round-bottom flask was purged with argon
  2. temperaturecooled to room temperature
  3. extractionThe aqueous layer was extracted three times with 100 ml chloroform
  4. washthe combined organic layers were washed three times with 100 ml water
  5. customThe organic solvent was evaporated
  6. customthe crude product was purified by flash chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-00124a126b114070a4139697ee5b43e7
出典データセット
uspto-grants-2004_03
特許番号
US06706528B2

関連ノート

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