Ethyl formate → HCID 20317093, compound

HRID 462017Notes

Reaction equation

HRID 462017 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[CH:11][N:10]([CH3:25])[CH:9]=1.ClC1C=CC=CC=1CC(=O)CC1C=CC=C(C(F)(F)F)C=1.C(OCC)=O.Cl.CN.N1C=CC=CC1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13](=[O:14])[CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:16]=2)[CH2:11][N:10]([CH3:25])[CH2:9]1

Participants

8

Reactant 7

HCID 8025Ethyl formateHCID 88712-PyridoneHCID 166653HydrideHCID 6364545Methylamine hydrochlorideHCID 12879242HCID 12879242, compoundHCID 203170851-(2-Chlorophenyl)-3-[3-(trifluoromethyl)phenyl]propan-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 20317093HCID 20317093, compound

Procedure

Ten g. of 3-(2-chlorophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinone was prepared from 35 g. of 1-(2-chlorophenyl)-3-(3-trifluoromethylphenyl)-2-propanone by reaction with ethyl formate and methylamine hydrochloride as described in Examples 1-3. The pyridinone was reduced with 2 g. of lithium aluminum hydride and excess hydride was decomposed and the product worked up and chromatographed as described in Examples 1-3. The recovered yields were about 1.3 g. of a mixture of the compounds of Examples 21 and 22, which were identified by mass spectroscopy with an indicated molecular weight of 365. About 2.1 g. of the compound of Example 23 was recovered, m.p. 90°-92°. The elemental analysis of Example 23 was as follows.

Workup

  1. customchromatographed
  2. customThe recovered yields
  3. customof the compound of Example 23 was recovered

Sources & evidence

ORD record
ord-78a1b7cc53574226b0624ab484109a46
Source dataset
uspto-grants-1977_12
Patent number
US04065290

Reaction notes

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