Hydrochloric Acid → HCID 9802058, compound

HRID 1595761Notes

Reaction equation

HRID 1595761 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.[NH2:21][C:22]1[CH:23]=[C:24]([C:32]([NH:34][NH2:35])=[O:33])[C:25](=[CH:30][CH:31]=1)[C:26](NN)=[O:27].C(=O)([O-])[O-].[Na+].[Na+].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.Cl>COCCO>[O:27]=[C:26]1[C:25]2[C:24](=[CH:23][C:22]([NH:21][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][CH:30]=2)[C:32](=[O:33])[NH:34][NH:35]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrileHCID 21704809HCID 21704809, compound

Product 1

HCID 9802058HCID 9802058, compound

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 273 mg (1.54 mM) of 4-Aminophthalhydrazide Hydrate 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 solution was made acetic by addition of concentrated HCl and the solid was collected, washed with water followed by ether and dried under vacuum at 80° C. The solid was taken up into 200 ml of methanol and 500 μl of 5 N sodium hydroxide and boiled for 20 minutes. To this heterogeneous mixture was added 100 ml of glacial acetic acid and the volume was reduced to a total of 100 ml by boiling. To the room temperature mixture, 500 ml of ice cold water was added and the solid was collected, washed with water followed by ether and dried under vacuum at 80° C. The solid was digested in 400 ml of ethanol until the volume had been reduced to 150 ml. The hot solution was filtered and the solid was washed with ethanol and to dried under vacuum at 80° C. yield 121 mg of the title compound as a white solid: mass spectrum (electrospray, m/e): M+H 418.0, mp=>270° C.

Workup

  1. customthe solid was collected
  2. washwashed with water
  3. customdried under vacuum at 80° C
  4. additionTo this heterogeneous mixture was added 100 ml of glacial acetic acid
  5. additionTo the room temperature mixture, 500 ml of ice cold water was added
  6. customthe solid was collected
  7. washwashed with water
  8. customdried under vacuum at 80° C
  9. filtrationThe hot solution was filtered
  10. washthe solid was washed with ethanol
  11. dry with materialto dried under vacuum at 80° C. yield 121 mg of the title compound as a white solid

Sources & evidence

ORD record
ord-2ff56cacd9804dd5b87e024219544fb1
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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