Sodium Carbonate → 3-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine

HRID 707343ノート

反応式

HRID 707343 の反応式
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:15][CH:14]([NH2:16])[CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:24]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=1>CN(C)C=O.O>[N+:30]([C:29]1[C:24]([NH:16][CH:14]2[CH2:13][N:12]([C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[N:2]=3)[CH2:15]2)=[N:25][CH:26]=[CH:27][CH:28]=1)([O-:32])=[O:31]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 67477378HCID 67477378、化合物

生成物 1

HCID 866942023-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine収率 85%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(quinolin-2-yl)azetidin-3-amine hydrochloride (0.90 g, 3.84 mmol) in dry dimethylformamide (15 mL) was added sodium carbonate (1.22 g, 11.5 mmol) and 2-chloro-3-nitro-pyridine (608 mg, 3.84 mmol). The reaction mixture was stirred and heated at reflux for 14 hours. The reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with water (30 mL), brine (30 mL), and dried over sodium sulfate. The filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel (20% to 50% ethyl acetate in petroleum ether) to give 3-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine (1.05 g, 3.20 mmol, 85% yield) as yellow solid.

後処理

  1. temperatureheated
  2. temperatureat reflux for 14 hours
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. washThe combined organic extracts were washed with water (30 mL), brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel (20% to 50% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-06a561d50d1f4eaa86b271f8937d63e6
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

反応ノート

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