Pyridine → HCID 9923792, compound

HRID 612177Notes

Reaction equation

HRID 612177 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:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][OH:23].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OC(O)C)C>[OH:23][CH2:22][C:21]1[CH:20]=[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])[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 802933-Aminobenzyl alcoholHCID 516892Sodium BicarbonateHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 9923792HCID 9923792, compound

Reagents, catalysts & solvents 1

HCID 101298981-EthoxyethanolSolvent

Procedure

A stirred mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile (7.46 g, 30 mmol), 3-aminobenzyl alcohol (7.39 g, 60 mmol), pyridine (2.43 ml, 30 mmol), and 90 ml of ethoxyethanol was refluxed for 5 h, cooled, and stirred with aqueous sodium bicarbonate. The resulting solid was filtered, washed with water, and dried. Recrystallization from methanol gave a brown solid, mp 250-255° C.

Workup

  1. temperaturewas refluxed for 5 h
  2. temperaturecooled
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried
  6. customRecrystallization from methanol
  7. customgave a brown solid, mp 250-255° C.

Sources & evidence

ORD record
ord-772e20343dbc4276a451aa887d44e7e5
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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