Methylamine → 3-Methoxyacetyl-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinone

HRID 2058873Notes

Reaction equation

HRID 2058873 reaction equation
[CH3:1][N:2]([CH3:23])[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:5](=[O:12])[CH2:6][C:7](=[O:11])[CH2:8][O:9][CH3:10].COC(OC)N(C)C.CN>>[CH3:10][O:9][CH2:8][C:7]([C:6]1[C:5](=[O:12])[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[CH:14]=2)=[CH:3][N:2]([CH3:1])[CH:23]=1)=[O:11]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 54463903HCID 54463903, compound

Product 1

HCID 132018213-Methoxyacetyl-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinone

Procedure

A 1 g. portion of impure 1-dimethylamino-6-methoxy-2-(3-trifluoromethylphenyl)-1-hexene-3,5-dione was reacted with 10 ml. of N,N-dimethylformamide dimethyl acetal, and then with 5 ml. of 40% aqueous methylamine, as described in Example 15. The product was purified as described in that example, except that 1:1 ethyl acetate:dichloromethane was used as the eluent, to obtain 0.13 g. of the desired product, m.p. 140°, dec. Nmr analysis in DMSOd6 showed peaks at δ7.6-8.5 (m, 6H, aromatic); 4.8 (s, 2H, COCH2); 3.9 (s, 3H, N--CH3); 3.4 (s, 3H, OCH3).

Workup

  1. customThe product was purified
  2. customto obtain 0.13 g

Sources & evidence

ORD record
ord-3b0496d7c09f484a821eeb4fc10985cd
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

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