Ethyl formate → HCID 20317077, compound

HRID 867040Notes

Reaction equation

HRID 867040 reaction equation
ClC1C=CC(CC(=O)CC2C=CC=C(C(F)(F)F)C=2)=CC=1.C(OCC)=O.Cl.CN.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[C:42](=[O:43])[C:41]([C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([F:53])([F:52])[F:51])[CH:45]=3)=[CH:40][N:39]([CH3:54])[CH:38]=2)=[CH:33][CH:32]=1.N1C=CC=CC1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([CH:37]2[C:42](=[O:43])[CH:41]([C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([F:53])([F:51])[F:52])[CH:45]=3)[CH2:40][N:39]([CH3:54])[CH2:38]2)=[CH:35][CH:36]=1

Participants

7

Reactant 6

HCID 8025Ethyl formateHCID 88712-PyridoneHCID 6364545Methylamine hydrochlorideHCID 12879239HCID 12879239, compoundHCID 21226445Aluminium lithium hydrideHCID 233457531-(4-Chlorophenyl)-3-[3-(trifluoromethyl)phenyl]propan-2-one

Product 1

HCID 20317077HCID 20317077, compound

Procedure

A 15 g. portion of 1-(4-chlorophenyl)-3-(3-trifluoromethylphenyl)-2-propanone was reacted with ethyl formate and methylamine hydrochloride to prepare 10 g. of 3-(4-chlorophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinone. The intermediate pyridinone was reduced with lithium aluminum hydride. Column chromatographic separation of the reaction mixture on a silica gel column as described in the examples above produced about 0.5 g. of the compound of Example 18, m.p. 122.5°, about 1.1 g. of the compound of Example 19, m.p. 113.5°, and about 1.3 g. of the compound of Example 20, m.p. 115.5°.

Workup

  1. customto prepare 10 g
  2. customColumn chromatographic separation of the reaction mixture on a silica gel column
  3. customabove produced about 0.5 g

Sources & evidence

ORD record
ord-e1f60e856d644e64b6ca20731c0ef979
Source dataset
uspto-grants-1978_07
Patent number
US04102669

Reaction notes

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