Water → N-Ethylpyridine-4-methylamine

HRID 874197ノート

反応式

HRID 874197 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH2:9]([NH2:11])[CH3:10].[BH4-].[Na+].O>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:11][CH2:9][CH3:10])=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 962WaterHCID 6341EthylamineHCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 96681N-Ethylpyridine-4-methylamine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

15.70 g (0.147 mol) of 4-pyridine-formaldehyde was dissolved in 200 mL of ethanol, added under stirring in cold-water-bath with 21 g (0.296 mol) of 65-70% ethylamine aqueous solution, reacted for 0.5 h, monitored with TLC until the reaction was almost completed. Added carefully with 5.6 g (0.148 mol) of sodium borohydride in several batches, small amount in each batch, after the end of addition, added with 30 mL of water, reacted overnight (20 h), the reaction was completed according to TLC monitoring. Evaporated to remove solvent, added with water, extracted with dichloromethane, washed with water and saturated saline in order, dried with anhydrous sodium sulfate, evaporated to remove solvent to obtain yellow thick liquid, 30 g, crude yield 73.4%. 1H NMR(CDCl3, 400 MHz)δ: 1.14(t, 3H, J=7.00 Hz), 2.66(q, 2H, J=7.00 Hz), 3.81(s, 2H), 7.26-7.27(m, 2H), 8.52-8.54(m, 2H).

後処理

  1. additionadded
  2. customreacted for 0.5 h
  3. additionafter the end of addition
  4. customreacted overnight (20 h)
  5. customEvaporated
  6. customto remove solvent
  7. additionadded with water
  8. extractionextracted with dichloromethane
  9. washwashed with water and saturated saline in order
  10. dry with materialdried with anhydrous sodium sulfate
  11. customevaporated
  12. customto remove solvent
  13. customto obtain yellow thick liquid, 30 g, crude yield 73.4%

出典と根拠

ORDレコード
ord-280a2856eaed4904b56db681a40302d7
出典データセット
uspto-grants-2015_03
特許番号
US08980887B2

反応ノート

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