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

HRID 1821091노트

반응식

HRID 1821091 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 7967Cyclohexanone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4232687616004c5a96b70b766c334f8d
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605265B2

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