Triphenylphosphine → HCID 22646612, compound

HRID 393620Notes

Reaction equation

HRID 393620 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:32][C:33]1[C:42]2[C:37](=[CH:38][C:39]([OH:45])=[C:40]([O:43][CH3:44])[CH:41]=2)[N:36]=[CH:35][CH:34]=1.[N:46]1[CH:51]=[CH:50][CH:49]=[C:48]([CH2:52][CH2:53][CH2:54]O)[CH:47]=1>C(Cl)Cl>[Cl:32][C:33]1[C:42]2[C:37](=[CH:38][C:39]([O:45][CH2:54][CH2:53][CH2:52][C:48]3[CH:47]=[N:46][CH:51]=[CH:50][CH:49]=3)=[C:40]([O:43][CH3:44])[CH:41]=2)[N:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 178613-PyridinepropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1355837314-Chloro-6-methoxyquinolin-7-ol

Product 1

HCID 22646612HCID 22646612, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (340 mg, 2 mmol) was added dropwise to a solution of triphenylphosphine (520 mg, 2 mmol), 4-chloro-7-hydroxy-6-methoxyquinoline (265 mg, 1.26mmol), (prepared as described for the starting material in Example 3), and 3-(3-pyridyl)-1-propanol (170 mg, 1.24 mmol) in methylene chloride (10 ml). The mixture was stirred for 1 hour at ambient temperature. The volatiles were removed by evaporation and the residue was purified by column chromatography eluting with methylene chloride/acetonitrile/methanol (50/45/5 increasing to 50/40/10). The purified product was triturated with ether, collected by filtration and dried under vacuum to give 4-chloro-6-methoxy-7-(3-(3-pyridyl)propoxy)quinoline (300 mg, 72%).

Workup

  1. custom(prepared
  2. customThe volatiles were removed by evaporation
  3. customthe residue was purified by column chromatography
  4. washeluting with methylene chloride/acetonitrile/methanol (50/45/5 increasing to 50/40/10)
  5. customThe purified product was triturated with ether
  6. filtrationcollected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-4de492b5ce7541048683216fee981681
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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