4-Amino-2,6-dichlorophenol → HCID 5328858, compound

HRID 1935105Notes

Reaction equation

HRID 1935105 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]=[C:23]([Cl:25])[C:22]([OH:26])=[C:21]([Cl:27])[CH:20]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:25][C:23]1[CH:24]=[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:20]=[C:21]([Cl:27])[C:22]=1[OH:26]

Participants

5

Reactant 3

HCID 800374-Amino-2,6-dichlorophenolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 5328858HCID 5328858, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A reaction mixture of 248.7 mg (1 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 213.6 mg (1.2 mmol) of 4-amino-2,6-dichlorophenol and 115.6 mg (1 mmol) of pyridine hydrochloride in 10 mL of 2-ethoxyethanol was refluxed under N2 for 1 hr. After removal of the solvent, the residue was diluted with water and neutralized to pH 7-8 with diluted sodium carbonate solution. The precipitate was filtered and washed with water and ether/ ethyl acetate (1:1). After drying in vacuo this yielded 346.7 mg (88.8%) of the product as a yellow solid, m.p.>250° C., mass (electrospray, m/e): M+H 389.8, 391.8.

Workup

  1. temperaturewas refluxed under N2 for 1 hr
  2. customAfter removal of the solvent
  3. additionthe residue was diluted with water and neutralized to pH 7-8 with diluted sodium carbonate solution
  4. filtrationThe precipitate was filtered
  5. washwashed with water and ether/ ethyl acetate (1:1)
  6. dry with materialAfter drying in vacuo this yielded 346.7 mg (88.8%) of the product as a yellow solid, m.p.>250° C., mass (electrospray, m/e)

Sources & evidence

ORD record
ord-e4447396219b4732a33f0ce584ab3122
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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