Sodium Carbonate → HCID 21956430, compound

HRID 989298Notes

Reaction equation

HRID 989298 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:15])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[NH2:23].Cl.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCCO)C.O>[Cl:15][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:23][C:22]3[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:20]([O:19][CH3:18])[CH:21]=3)=[C:3]([C:16]#[N:17])[CH:4]=[N:5]2)=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 322853,4,5-TrimethoxyanilineHCID 10176127Pyridinium chlorideHCID 219564524,7-Dichloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 21956430HCID 21956430, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 500 mg (1.86 mmol) of 4,7-dichloro-6-nitro-3-quinolinecarbonitrile, 342.0 mg (1.86 mmol) of 3,4,5-trimethoxyaniline and 215.5 mg (1.86 mmol) of pyridine hydrochloride in 25 mL of 2-ethoxyethanol is heated at 100-110° C. for 1.5 hours. After cooling, the mixture is diluted with water and neutralized with an aqueous solution of saturated sodium carbonate. The solid is collected by filtration and is washed with water. After drying in vacuo, this yields 621.0 mg (80.5%) of the product as a deep yellow solid.

Workup

  1. temperatureAfter cooling
  2. filtrationThe solid is collected by filtration
  3. washis washed with water
  4. customAfter drying in vacuo

Sources & evidence

ORD record
ord-7c117937bfc24df0a5a1f5b248aba7a8
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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