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Toluene → 2-Amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile

HRID 392182
Notes
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Reaction equation

HRID 392182 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7].[CH2:15]1[CH2:25][C:23](=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1.C([O-])(=O)C.[NH4+:30].C1(C)C=CC=CC=1>C(OCC)(=O)C>[NH2:9][C:8]1[C:5]([C:6]#[N:7])=[C:4]([C:3]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:2]=2[Cl:1])[C:25]2[CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[C:23]=2[N:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 107241-TetraloneHCID 180892,4-DichlorobenzylidenemalononitrileHCID 517165Ammonium Acetate

Product 1

HCID 226635122-Amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrileYield 47.4%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

A mixture of 2-(2,4-dichloro-benzylidene)-malononitrile (1.125 g, 5 mmol), alpha-tetralone (735 mg, 5 mmol), ammonium acetate (578 mg, 7.5 mmol), and toluene (5 ml) was stirred for 3 h at reflux. Upon cooling to room temperature, the mixture was taken up in ethyl acetate and extracted with satd. NaHCO3, water, and satd. NaCl, and dried over Na2SO4. The solvent was then evaporated and the title compound (868 mg, 47%), MS: m/e=365.9 (M+H+), was isolated from the residue by column chromatography (silica gel, hexanes, ethyl acetate).

Workup

  1. temperatureat reflux
  2. extractionextracted with satd
  3. dry with materialNaCl, and dried over Na2SO4
  4. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-db123ef6cc7941fa984100ea1f66978f
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06800650B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes