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

HRID 1821091Notes

Reaction equation

HRID 1821091 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7967CyclohexanoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4232687616004c5a96b70b766c334f8d
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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