Pyridine → HCID 5328848, compound

HRID 1935089Notes

Reaction equation

HRID 1935089 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:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1.N1C=CC=CC=1.C(OC(O)C)C.C(=O)(O)[O-].[Na+]>>[NH2:18][C:19]1[CH:20]=[C:21]([NH:25][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])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 5

HCID 1049PyridineHCID 7935M-PhenylenediamineHCID 516892Sodium BicarbonateHCID 101298981-EthoxyethanolHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 5328848HCID 5328848, compound

Procedure

A stirred mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile (3.73 g, 15 mmol), 1,3-diaminobenzene (4.86 g, 45 mmol), pyridine (1.21 ml, 15 mmol), and 45 ml of ethoxyethanol was refluxed for 30 m, cooled,and stirred with aqueous sodium bicarbonate. The resulting solid was filtered, washed with water, and dried. Recrystallization from ethanol gave a brown solid, mp 222-228° C.

Workup

  1. temperaturewas refluxed for 30 m
  2. filtrationThe resulting solid was filtered
  3. washwashed with water
  4. customdried
  5. customRecrystallization from ethanol
  6. customgave a brown solid, mp 222-228° C.

Sources & evidence

ORD record
ord-ff4de7ed3e634166b726f2a4d4b0565a
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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