2-[(2,3-Dimethylphenoxy)methyl]oxirane → HCID 13506762, compound

HRID 1583440Notes

Reaction equation

HRID 1583440 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:13]2[C:12](=[O:22])[CH2:11][NH:10][CH2:9][C:8]=2[NH:7][C:6]=1[CH3:23])=[O:4].[CH3:24][C:25]1[C:35]([CH3:36])=[CH:34][CH:33]=[CH:32][C:26]=1[O:27][CH2:28][CH:29]1[O:31][CH2:30]1>CO>[CH3:1][O:2][C:3]([C:5]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:13]2[C:12](=[O:22])[CH2:11][N:10]([CH2:30][CH:29]([OH:31])[CH2:28][O:27][C:26]3[CH:32]=[CH:33][CH:34]=[C:35]([CH3:36])[C:25]=3[CH3:24])[CH2:9][C:8]=2[NH:7][C:6]=1[CH3:23])=[O:4]

Participants

4

Reactant 2

HCID 126196772-[(2,3-Dimethylphenoxy)methyl]oxiraneHCID 12818458HCID 12818458, compound

Product 1

HCID 13506762HCID 13506762, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,4,5,6,7,8-Hexahydro-2-methyl-4-(2-methylphenyl)-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester (14.5 g), 6.8 g of 3-(2,3-dimethylphenoxy)-1,2-epoxypropane and 250 ml of methanol were combined and refluxed for 18 hours. The solvent was removed in vacuo. The residue was dissolved in diethyl ether and saturated with hydrogen chloride. The solid was separated and dried in vacuo at 75° C. for 18 hours. The solid was recrystallized from acetonitrile to obtain 7.7 g of the title compound as the hydrochloride salt, m.p. 220° C. dec.

Workup

  1. temperaturerefluxed for 18 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in diethyl ether and saturated with hydrogen chloride
  4. customThe solid was separated
  5. customdried in vacuo at 75° C. for 18 hours
  6. customThe solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-220563bc64f346139d61676428fe3e7a
Source dataset
uspto-grants-1985_11
Patent number
US04551534

Reaction notes

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