Pyridine → HCID 9949239, compound

HRID 654145Notes

Reaction equation

HRID 654145 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([CH3:17])[CH:13]2[O:14][CH:12]2[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:15]#[N:16])[CH:10]=2)[O:5]1.[NH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]1=[O:24].N1C=CC=CC=1>C(O)C>[CH3:1][O:2][CH2:3][C:4]1([CH3:17])[CH:13]([OH:14])[CH:12]([N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]2=[O:24])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:15]#[N:16])[CH:10]=2)[O:5]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 88712-PyridoneHCID 15056482HCID 15056482, compound

Product 1

HCID 9949239HCID 9949239, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 23.1 g of 2-methoxymethyl-2-methyl3,4-epoxy-6-cyanochroman, 9.5 g of 1H-2-pyridone, 12 ml of pyridine and 600 ml of ethanol is boiled for 72 hours. About 300 ml are removed by distillation, the mixture is cooled and filtered, the solution is evaporated and the residue is worked up in the customary manner. 2-Methoxymethyl-2-methyl-4-(1,2-dihydro-2-oxo-1-pyridyl)-6-cyano3-chromanol, stereoisomer mixture ("A") is obtained, which can be separated into isomer "Al" (CH3 and OH in the cis-position; m.p. 216°-218° C.) and isomer "A2" (CH3 and OH in the trans-position; m.p. 210°-212° C.) by chromatography (silica gel; ethyl acetate/methanol).

Workup

  1. customAbout 300 ml are removed by distillation
  2. temperaturethe mixture is cooled
  3. filtrationfiltered
  4. customthe solution is evaporated

Sources & evidence

ORD record
ord-8daea981b1d345d9af4d122ca9a78e8b
Source dataset
uspto-grants-1992_07
Patent number
US05130322

Reaction notes

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