Benzonitrile, 2-amino-4-chloro- → 9-AMINO-6-CHLORO-1,2,3,4-TETRAHYDRO-ACRIDINE

HRID 1821091ノート

反応式

HRID 1821091 の反応式
[NH2:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>[Cl-].[Zn+2].[Cl-].C1(=O)CCCCC1>[Cl:10][C:8]1[CH:9]=[C:2]2[C:3](=[CH:6][CH:7]=1)[C:4]([NH2:5])=[C:3]1[C:2]([CH2:9][CH2:8][CH2:7][CH2:6]1)=[N:1]2

参加物

4

反応物 1

HCID 170059Benzonitrile, 2-amino-4-chloro-

生成物 1

HCID 103990689-AMINO-6-CHLORO-1,2,3,4-TETRAHYDRO-ACRIDINE収率 99.7%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 7967Cyclohexanone溶媒

実験手順

2-Amino-4-chlorobenzonitrile (5.0 g, 33 mmolL), cyclohexanone (30 ml) and Zinc chloride (4.8 g, 35 mmoL) were mixed in a round bottomed flask and heated up to 120 degree Celsius for 3 hours. After cooling to room temperature, the solvent was decanted off. The resulting residue was triturated with ethyl acetate (30 ml). The solid was collected by filtration and added into 10% aqueous NaOH (50 ml). After stiring for 2 hours, the mixture was filtered and the filter cake was washed thoroughly with water. The filter cake was then extracted with methanol. The combined methanolic extract was concentrated to produce the desired product (3.8 g, 16 mmoL) in 48% yield.

後処理

  1. temperatureheated up to 120 degree Celsius for 3 hours
  2. customthe solvent was decanted off
  3. customThe resulting residue was triturated with ethyl acetate (30 ml)
  4. filtrationThe solid was collected by filtration
  5. additionadded into 10% aqueous NaOH (50 ml)
  6. filtrationthe mixture was filtered
  7. washthe filter cake was washed thoroughly with water
  8. extractionThe filter cake was then extracted with methanol
  9. extractionThe combined methanolic extract
  10. concentrationwas concentrated

出典と根拠

ORDレコード
ord-4232687616004c5a96b70b766c334f8d
出典データセット
uspto-grants-2009_10
特許番号
US07605265B2

反応ノート

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