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Methanol → 4-(2,4-Dichloroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile

HRID 2213723
Notes
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Reaction equation

HRID 2213723 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][C:20]=3[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:31]#[N:32].CO>CN(C=O)C.O.C(OCC)C>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:13]1[C:22]2[C:17](=[CH:18][C:19]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][C:20]=3[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:31]#[N:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 887MethanolHCID 111232,4-DichloroanilineHCID 24758Sodium hydrideHCID 99441164-Chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile

Product 1

HCID 102959004-(2,4-Dichloroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrileYield 59.5%

Reagents, catalysts & solvents 3

HCID 3283
Diethyl Ether
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Procedure

A mixture of 178.2 mg (1.1 mmol) of 2,4-dichloroaniline and 44.0 mg (1.1 mmol) of sodium hydride in anhydrous DMF is stirred at room temperature for 0.5 hours. To the mixture is added 149.4 mg (0.5 mmol) of 4-chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile. The resulting mixture is heated at 50–60° C. for 1 hour. After cooling, the mixture is diluted with water and extracted with ethyl acetate. The organic phase is washed with brine and dried over sodium sulfate. Removal of the solvent yields a dark residue which is purified on preparative TLC (developing solvent: 97:3 methylene chloride/methanol), giving a yellow foam. Trituration of the foam with diethyl ether containing several drops of methanol yields 126.1 mg (59.5%) of the product as a yellow solid, mp 271–273° C.

Workup

  1. temperatureThe resulting mixture is heated at 50–60° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent
  7. customyields a dark residue which
  8. customis purified on preparative TLC (developing solvent: 97:3 methylene chloride/methanol)
  9. customgiving a yellow foam

Sources & evidence

ORD record
ord-985c6933486047f2b25b1ae25e6a339d
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07105531B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes