Sodium Carbonate → HCID 10293832, compound

HRID 1595760Notes

Reaction equation

HRID 1595760 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].[O:20]1[C:25]2[CH:26]=[CH:27][C:28]([NH2:30])=[CH:29][C:24]=2[O:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCO>[O:20]1[C:25]2[CH:26]=[CH:27][C:28]([NH:30][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:29][C:24]=2[O:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 891481,4-Benzodioxan-6-ylamineHCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrile

Product 1

HCID 10293832HCID 10293832, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 232 mg (1.54 mM) of 1,4-Benzodioxane-6-amine in 15 ml of 2-methoxyethanol 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-(2,3-Dihydro-benzo[1,4]dioxin-6-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile as a yellow solid: mass spectrum (electrospray, m/e): M+H 402.9, mp=225-227° C.

Workup

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

Sources & evidence

ORD record
ord-a887fa373b6b46dabff794cec5b3a99b
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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