4-Chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile → 4-(4-Chloro-5-methoxy-2-methylanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile

HRID 989290Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:20]#[N:21].[Cl:22][C:23]1[C:29]([O:30][CH3:31])=[CH:28][C:26]([NH2:27])=[C:25]([CH3:32])[CH:24]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:22][C:23]1[C:29]([O:30][CH3:31])=[CH:28][C:26]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][C:8]4[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=4[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:20]#[N:21])=[C:25]([CH3:32])[CH:24]=1

Participants

Conditions

Temperature: 125 °C

Procedure

Following the procedure of Example 11, a mixture of 75.8 mg (0.25 mmol) of 4-chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile, 51.5 mg (0.30 mmol) of 4-chloro-5-methoxy-2-methylaniline and 28.9 mg (0.25 mmol) of pyridine hydrochloride in 5.0 mL of 2-ethoxyethanol is heated at 120-130° C. for 2 hours to yield the crude product. Purification of the crude product on preparative TLC (developing solvent: 95:5 methylene chloride/methanol) yields 88.7 mg (82.1%) of the pure product as a yellow solid, mp 171-173° C.

Workup

customto yield the crude product
customPurification of the crude product on preparative TLC (developing solvent: 95:5 methylene chloride/methanol)

Sources & evidence

ORD record: ord-0b2675c889a94bb1be051f275e8d7f46
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638929B2

Reaction notes

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