Pyridine → HCID 5328848, compound

HRID 612175Notes

Reaction equation

HRID 612175 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. temperaturecooled
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried
  6. customRecrystallization from ethanol
  7. customgave a brown solid, mp 222-228° C.

Sources & evidence

ORD record
ord-bc5f4f89ef56439b88a3870e890f7b6e
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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