Water → 4-Phenoxybutan-1-amine

HRID 2421956ノート

反応式

HRID 2421956 の反応式
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.O.CCOC(C)=O>CCO>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9321HydrazineHCID 166375972-(4-Phenoxybutyl)-1H-isoindole-1,3(2H)-dione

生成物 1

HCID 1162404-Phenoxybutan-1-amine収率 67%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-(4-phenoxybutyl)1H-isoindole-1,3(2H)-dione (10.10 g, 3.27 mmol) and 25% hydrazine solution in water (2.88 ml, 13.10 mmol) in EtOH (30 ml) was warmed at reflux. After 1.5 h, EtOAc was added and the mixture was extracted with brine. The combined aqueous phases were then re-extracted with EtOAc and all the organic phases combined. These were then extracted with 1N HCl, the acidic aqueous phases combined, basified with 2N NaOH and re-extracted into EtOAc before evaporating to dryness to give the title compound (0.411 mg, 67%) as an oil. 1H NMR (500 MHz CDCl3): δ 7.32-2.26 (m, 2H), 6.95 (t, 1H), 4.00 (t, 2H), 2.80 (t, 2H), 1.90-1.82 (m, 2H), 1.68-1.62 (m, 2H).

後処理

  1. temperaturewas warmed
  2. temperatureat reflux
  3. extractionthe mixture was extracted with brine
  4. extractionThe combined aqueous phases were then re-extracted with EtOAc and all the organic phases
  5. extractionThese were then extracted with 1N HCl
  6. extractionre-extracted into EtOAc
  7. custombefore evaporating to dryness

出典と根拠

ORDレコード
ord-3e32c09772a5498ab7fd2c1babc4d3c2
出典データセット
uspto-grants-2011_06
特許番号
US07960380B2

反応ノート

読み込み中…