Hydrochloric Acid → 4-(8-Hydroxy-quinolin-5-ylamino)-6,7-dimethoxy-quinoline-3-carbonitrile

HRID 1595785Notes

Reaction equation

HRID 1595785 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+].Cl>O.N1C=CC=CC=1>[OH:29][C:26]1[CH:27]=[CH:28][C:19]([NH:18][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]#[N:17])=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 4160025-Amino-8-hydroxyquinolineHCID 101298981-EthoxyethanolHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 99476494-(8-Hydroxy-quinolin-5-ylamino)-6,7-dimethoxy-quinoline-3-carbonitrileYield 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.233 g of 5-amino-8-hydroxyquinoline dihydrocholride, 0.158 g of pyridine, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 2 hours. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate and concentrated hydrochloric acid to adjust pH to 7. The product was collected, washed with water, and dried to give 0.210 g of 4-(8-hydroxy-quinolin-5-ylamino)-6,7-dimethoxy-quinoline-3-carbonitrile as a solid, mp 150° C. (decomposed); mass spectrum (EI, m/e): M 372.1228.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-34f0879a7bfd432492419cad14816d57
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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