2-[(2,3-Dimethylphenoxy)methyl]oxirane → HCID 13506768, compound

HRID 1583441Notes

Reaction equation

HRID 1583441 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[C:17]([Cl:22])[C:16]=2[Cl:23])[C:13]2[C:12](=[O:24])[CH2:11][NH:10][CH2:9][C:8]=2[NH:7][C:6]=1[CH3:25])=[O:4].[CH3:26][C:27]1[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:28]=1[O:29][CH2:30][CH:31]1[O:33][CH2:32]1>CO.Cl>[CH3:1][O:2][C:3]([C:5]1[CH:14]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[C:17]([Cl:22])[C:16]=2[Cl:23])[C:13]2[C:12](=[O:24])[CH2:11][N:10]([CH2:32][CH:31]([OH:33])[CH2:30][O:29][C:28]3[CH:34]=[CH:35][CH:36]=[C:37]([CH3:38])[C:27]=3[CH3:26])[CH2:9][C:8]=2[NH:7][C:6]=1[CH3:25])=[O:4]

Participants

5

Reactant 2

HCID 126196772-[(2,3-Dimethylphenoxy)methyl]oxiraneHCID 70490064HCID 70490064, compound

Product 1

HCID 13506768HCID 13506768, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

4-(2,3-Dichloro-6-fluorophenyl)-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester (12.1 g), 5.3 g of 3-(2,3-dimethylphenoxy)-1,2-epoxypropane and 150 ml of methanol were combined and refluxed for 18 hours. The alcohol was evaporated in vacuo. The residue was chromatographed on silica-gel using a 5% methanol-ethyl acetate system. The residue obtained on evaporation was dissolved in methanol and saturated with hydrogen chloride. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. A precipitate formed on standing at room temperature. The solid was separated and treated with boiling acetonitrile. The solid was dried in vacuo to obtain 2.8 g of the title compound as the hydrochloride salt, m.p. 190°-3° C.

Workup

  1. temperaturerefluxed for 18 hours
  2. customThe alcohol was evaporated in vacuo
  3. customThe residue was chromatographed on silica-gel
  4. customThe residue obtained on evaporation
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. customA precipitate formed
  8. customon standing at room temperature
  9. customThe solid was separated
  10. additiontreated with boiling acetonitrile
  11. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-4355266d43dd4e3a86a1977d7e5b7d1f
Source dataset
uspto-grants-1985_11
Patent number
US04551534

Reaction notes

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