2-(Dimethylamino)ethanol → 2-(2-Dimethylaminoethoxy)-5-nitropyridine

HRID 1512100ノート

反応式

HRID 1512100 の反応式
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1>CN(C=O)C.O.CCOC(C)=O>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:19][CH:20]=1)([O-:26])=[O:25]

参加物

7

反応物 3

HCID 79022-(Dimethylamino)ethanolHCID 783082-Chloro-5-nitropyridineHCID 2724254Sodium bis(trimethylsilyl)amide

生成物 1

HCID 529049082-(2-Dimethylaminoethoxy)-5-nitropyridine収率 44.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Microwave heating. To a solution of 2-(dimethylamino)ethanol (339 mg, 3.80 mmol) in DMF (5 mL) was added sodium bis(trimethylsilyl)amide (4.75 mL, 1M solution in THF, 4.75 mmol). The mixture was stirred at room temperature for 15 min. 2-Chloro-5-nitropyridine (500 mg, 3.16 mmol) was then added. The vial was capped and subjected to microwave irradiation (150° C. for 10 minutes). The mixture was diluted with water (250 mL) and EtOAc (250 mL). The two layers were separated, and the aqueous layer extracted two more times with EtOAc. The organic extracts were combined, washed with water and brine, dried over sodium sulfate and evaporated to give the crude material as brown oil. Purification by column chromatography on silica gel using 5% methanol/methylene chloride yielded 2-(5-nitropyridin-2-yloxy)-N,N-dimethylethanamine as a light yellow solid (295 mg, 44%).

後処理

  1. temperatureMicrowave heating
  2. customThe vial was capped
  3. customsubjected to microwave irradiation (150° C. for 10 minutes)
  4. customThe two layers were separated
  5. extractionthe aqueous layer extracted two more times with EtOAc
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto give the crude material as brown oil
  10. customPurification by column chromatography on silica gel using 5% methanol/methylene chloride

出典と根拠

ORDレコード
ord-54e7667f7ee14757bf3af95592da0362
出典データセット
uspto-grants-2012_07
特許番号
US08217035B2

反応ノート

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