Sodium Carbonate → HCID 9952290, compound

HRID 1595764Notes

Reaction equation

HRID 1595764 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:30]=[C:29]2[C:24]([CH2:25][O:26][C:27]2=[O:28])=[CH:23][CH:22]=1.Cl.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCO>[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:15][CH2:16][CH3:17])[N:5]=[CH:4][C:3]([C:18]#[N:19])=[C:2]2[NH:20][C:21]1[CH:30]=[C:29]2[C:24](=[CH:23][CH:22]=1)[CH2:25][O:26][C:27]2=[O:28])[CH3:14]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 936316-AminophthalideHCID 10176127Pyridinium chlorideHCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrile

Product 1

HCID 9952290HCID 9952290, compoundYield 95%

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, 230 mg (1.54 mM) of 6-Aminophthalide and 161 mg of pyridine hydrochloride in 12 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 535 mg of 6,7-Diethoxy-4-(3-oxo-1,3-dihydro-isobenzofuran-5-ylamino)-quinoline-3-carbonitrile as a white solid: mass spectrum (electrospray, m/e): M+H 390.1, mp=280-284° C.

Workup

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

Sources & evidence

ORD record
ord-b4b9a653e7b64246bce28b66142040a9
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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