4-Chlorobenzo[g]quinoline-3-carbonitrile → 4-(4-Chloro-5-methoxy-2-methylanilino)benzo[g]quinoline-3-carbonitrile

HRID 2213718Notes

Reaction equation

HRID 2213718 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[Cl:18][C:19]1[C:25]([O:26][CH3:27])=[CH:24][C:22]([NH2:23])=[C:21]([CH3:28])[CH:20]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:18][C:19]1[C:25]([O:26][CH3:27])=[CH:24][C:22]([NH:23][C:2]2[C:11]3[C:6](=[CH:7][C:8]4[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=4[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]#[N:17])=[C:21]([CH3:28])[CH:20]=1

Participants

5

Reactant 3

HCID 98346304-Chlorobenzo[g]quinoline-3-carbonitrileHCID 10176127Pyridinium chlorideHCID 123258794-Chloro-5-methoxy-2-methylaniline

Product 1

HCID 101773794-(4-Chloro-5-methoxy-2-methylanilino)benzo[g]quinoline-3-carbonitrileYield 72.2%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Following the procedure of Example 3, the reaction mixture of 141.8 mg (0.60 mmol) of 4-chlorobenzo[g]quinoline-3-carbonitrile, 102.9 mg (0.60 mmol) of 4-chloro-5-methoxy-2-methylaniline (can be prepared by the procedure disclosed in WO 85/01939, which is hereby incorporated by reference) and 57.8 mg (0.50 mmol) of pyridine hydrochloride in 8.0 mL of 2-ethoxyethanol is heated at 130–135° C. for 1.5 hours to yield the crude product. Purification of the crude product on preparative TLC (developing solvent: 95:5 methylene chloride/methanol) yields 159.3 mg (72.2%) of the pure product as a yellow solid, mp 195–197° C.

Workup

  1. customcan be prepared by the procedure
  2. temperatureis heated at 130–135° C. for 1.5 hours
  3. customto yield the crude product
  4. customPurification of the crude product on preparative TLC (developing solvent: 95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-433a908362f44a2d86a9791b7e0a3aa9
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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