(4-Aminophenoxy)benzene → HCID 23498106, compound

HRID 1837378Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:21]#[N:22].[O:23]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)[N:5]=[CH:4][C:3]([C:21]#[N:22])=[C:2]2[NH:34][C:33]1[CH:32]=[CH:31][C:30]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A reaction mixture of 0.12 g (0.38 mmol) of 4-chloro-6-methoxy-7-(4-methylpiperazin-1-yl)-quinoline-3-carbonitrile, 0.077 g (0.42 mmol) of 4-phenoxyaniline and 0.044 g (0.38 mmol) of pyridine hydrochloride in 2 ml of 2-ethoxyethanol is heated at 115° C. for 45 minutes. After cooling, the mixture is filtered, washed with cold 2-ethoxyethanol, then ethyl acetate. After drying in vacuo, the solid is suspended in a saturated solution of sodium carbonate, stirred for 45 minutes and collected by filtration. The reaction product is washed with water and dried in vacuo, to provide 0.11 g of 6-methoxy-7-(4-methylpiperazin-1-yl)-4-(4-phenoxyphenylamino)-quinoline-3-carbonitrile as a yellow solid, mp softens at 93° C.

Workup

temperatureAfter cooling
filtrationthe mixture is filtered
washwashed with cold 2-ethoxyethanol
customAfter drying in vacuo
filtrationcollected by filtration
washThe reaction product is washed with water
customdried in vacuo

Sources & evidence

ORD record: ord-50f203e540f746af9187eebe592864a9
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780996B2

Reaction notes

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