Sodium Carbonate → 4-(Benzo[1,3]dioxol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile

HRID 1595753Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[CH2:20]1[O:29][C:28]2[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=2[O:21]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[O:29]1[C:28]2[CH:27]=[CH:26][C:24]([NH:25][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=4)[N:5]=[CH:4][C:3]=3[C:18]#[N:19])=[CH:23][C:22]=2[O:21][CH2:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 258 mg (1.88 mM) of 3,4-(methylenedioxy) aniline in 10 ml of ethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100° C., then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80° C. to yield 526 mg of 4-(Benzo[1,3]dioxol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile as a tan solid: mass spectrum (electrospray, m/e): M+H 378.0, mp=200-203° C.

Workup

customThe solid was collected
washwashed with water
customdried under vacuum at 80° C.

Sources & evidence

ORD record: ord-ac14742b660a4e0fb012222bf7b51f6c
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288082B1

Reaction notes

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