Sodium Iodide → 8-(4-Methylpiperazin-1-yl)naphthalen-2-ol

HRID 399449

反応式

HRID 399449 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.C(=O)(O)[O-].[Na+].[I-].[Na+].[CH3:20][N:21]([CH2:25][CH2:26]Cl)[CH2:22][CH2:23]Cl.Cl.[OH-].[NH4+].C1C=CC2C(=CC=CC=2O)C=1>C(#N)C.CO.C(Cl)Cl>[CH3:20][N:21]1[CH2:25][CH2:26][N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]3)[CH2:23][CH2:22]1

参加物

10

反応物 6

HCID 5238Sodium IodideHCID 5935Nitrogen mustard hydrochlorideHCID 70051-NaphtholHCID 83588-Amino-2-naphthalenolHCID 14923Ammonium HydroxideHCID 516892Sodium Bicarbonate

生成物 1

HCID 108002178-(4-Methylpiperazin-1-yl)naphthalen-2-ol

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirring solution of 8-amino-2-naphthol (3.28 g, 20 mmol, Aldrich Chem. Co.) in 100 mL of acetonitrile was added sodium bicarbonate (7.42 g, 88 mmol), sodium iodide (6.72 g, 44 mmol) and mechlorethamine hydrochloride (4.32 g, 22 mmol). Under nitrogen, the reaction was heated to reflux and stirred for another 2 hr. The reaction mixture was then allowed to cool to room temperature and was stirred overnight. A thin layer chromatography (tlc) using methylene chloride: methanol: conc. ammonium hydroxide (90:10:1) showed the more polar product (Rf 0.25) with only a trace of the starting naphthol. Silica gel (4.5 g) was added and the reaction mixture was concentrated in vacuo to a dry purple solid. This was added to a column of silica gel (ca. 400 g) and eluted with 2 L volumes of CH2Cl2, CH2Cl2 :CH3OH (40:1), CH2Cl2 :CH3OH:conc. NH4OH (20:1:0.1) and finally 4 L of CH2Cl2 :CH3OH:conc. NH4CH (10:1:0.1). The appropriate fractions were combined to yield a purple-black solid, 5.26 g, mp 184°-185° C.

後処理

  1. temperatureUnder nitrogen, the reaction was heated
  2. temperatureto reflux
  3. stirringwas stirred overnight
  4. additionSilica gel (4.5 g) was added
  5. concentrationthe reaction mixture was concentrated in vacuo to a dry purple solid
  6. additionThis was added to a column of silica gel (ca. 400 g)
  7. washeluted with 2 L volumes of CH2Cl2, CH2Cl2 :CH3OH (40:1), CH2Cl2
  8. customto yield a purple-black solid, 5.26 g, mp 184°-185° C.

出典と根拠

ORDレコード
ord-347a497a622b47bc996cee0da2273737
出典データセット
uspto-grants-1998_10
特許番号
US05821245

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