Triphenylphosphine → 4-Chloro-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline

HRID 393642

Reaction equation

HRID 393642 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:26])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][CH:15]=1.[N:27]1([CH2:32][CH2:33]O)[CH:31]=[N:30][CH:29]=[N:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH2:33][CH2:32][N:27]3[CH:31]=[N:30][CH:29]=[N:28]3)=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5509251H-1,2,4-Triazole-1-ethanolHCID 1355837314-Chloro-6-methoxyquinolin-7-ol

Product 1

HCID 226465544-Chloro-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinolineYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (1 ml, 6.5 mmol) was added dropwise to a solution of 4-chloro-7-hydroxy-6-methoxyquinoline (845 mg, 4.0 mmol), (prepared as described for the starting material in Example 3), 2-([1,2,4]-triazol-1-yl)ethanol (500 mg, 4.4 mmol), (Ann. Pharm. Fr. 1977, 35, 503-508), and triphenylphosphine (1.7 g, 6.5 mmol) in methylene chloride (40 ml) under argon. After stirring for 4 days at ambient temperature, the insoluble materials were removed by filtration. The volatiles were removed by evaporation and the residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (75/20/5). The product was purified by a second chromatography on neutral alumina eluting with methylene chloride/acetonitrile/methanol (75/20/5). The purified product was triturated with ether, collected by filtration and dried under vacuum to give 4-chloro-6-methoxy-7-(2-([1,2,4]-triazol-1-yl)ethoxy)quinoline (544 mg, 45%).

Workup

  1. custom(prepared
  2. customthe insoluble materials were removed by filtration
  3. customThe volatiles were removed by evaporation
  4. customthe residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (75/20/5)
  5. customThe product was purified by a second chromatography on neutral alumina eluting with methylene chloride/acetonitrile/methanol (75/20/5)
  6. customThe purified product was triturated with ether
  7. filtrationcollected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-8d3f5f227766422fabf12c317ca2b63e
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Linked notes

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