Sodium Carbonate → 4-(1,1-Dioxo-1H-benzo[b]thiophen-6-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile

HRID 1595765Notes

Reaction equation

HRID 1595765 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].[NH2:20][C:21]1[CH:22]=[CH:23][C:24]2[CH:28]=[CH:27][S:26](=[O:30])(=[O:29])[C:25]=2[CH:31]=1.Cl.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCO.CCCCCC.CC(C)=O>[O:29]=[S:26]1(=[O:30])[CH:27]=[CH:28][C:24]2[CH:23]=[CH:22][C:21]([NH:20][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:31][C:25]1=2

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27798556-Amino-1,1-dioxobenzo(b)thiopheneHCID 10176127Pyridinium chlorideHCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrile

Product 1

HCID 98450934-(1,1-Dioxo-1H-benzo[b]thiophen-6-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 80192-MethoxyethanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile, 230 mg (1.54 mM) of 6-Amino-1,1-dioxobenzo[b]thiophene and 161 mg of pyridine hydrochloride in 12 ml of 2-methoxyethanol was refluxed for 6 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. The solid was dissolved in acetone and dried onto silica gel under high vacuum. Purification of the compound was obtained by chromatography using a gradient of 30% to 50% acetone in hexane. The first of the three components of the mixture isolated from the column was the desired product. Removal of the solvent by evaporation yielded 69 mg of 4-(1,1-Dioxo-1H-benzo[b]thiophen-6-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile as a yellow solid: mass spectrum (electrospray, m/e): M+H 421.9, mp=155-160° C.

Workup

  1. customThe solid was collected
  2. washwashed with water
  3. customdried under vacuum at 80° C
  4. dissolutionThe solid was dissolved in acetone
  5. customdried onto silica gel under high vacuum
  6. customPurification of the compound
  7. customwas obtained by chromatography
  8. customThe first of the three components of the mixture isolated from the column

Sources & evidence

ORD record
ord-22e4db505ad841ae86e057badd6ccdec
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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