Acetone → 2-chloro-N-[3-(3-chlorobenzoyl)-6-formylpyridin-2-yl]-N-ethylacetamide

HRID 1582973Notes

Reaction equation

HRID 1582973 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([C:7]1[C:8]([NH:18][CH2:19][CH3:20])=[N:9][C:10]([CH:13]([O:16]C)OC)=[CH:11][CH:12]=1)=[O:6].[ClH:24].[CH3:25][C:26](C)=[O:27]>>[Cl:24][CH2:25][C:26]([N:18]([C:8]1[C:7]([C:5](=[O:6])[C:4]2[CH:21]=[CH:22][CH:23]=[C:2]([Cl:1])[CH:3]=2)=[CH:12][CH:11]=[C:10]([CH:13]=[O:16])[N:9]=1)[CH2:19][CH3:20])=[O:27]

Participants

4

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 227166793-(3-Chlorobenzoyl)-2-ethylamino-6-dimethoxymethylpyridine

Product 1

HCID 227167072-chloro-N-[3-(3-chlorobenzoyl)-6-formylpyridin-2-yl]-N-ethylacetamide

Conditions

Temperature
60 °C

Procedure

To an acetone solution of 3-(3-chlorobenzoyl)-6-dimethoxymethyl-2-ethylaminopyridine was added 6M hydrochloric acid, and the whole was reacted at room temperature for 5 hours. After removal of the solvent by evaporation, propylene oxide and chloroacetyl chloride were added to the product obtained by a usual liquid-separation treatment in methyl t-butyl ether, and the whole was stirred at 60° C. for 14 hours. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain 2-chloro-N-[3-(3-chlorobenzoyl)-6-formylpyridin-2-yl]-N-ethylacetamide as a yellow oily substance. NMR1: 10.1 (1H, d, J=0.6 Hz), 7.95 (2H, brs), 1.0-1.5 (3H, m).

Workup

  1. customthe whole was reacted at room temperature for 5 hours
  2. customAfter removal of the solvent
  3. customby evaporation, propylene oxide and chloroacetyl chloride
  4. additionwere added to the product
  5. customobtained by a usual liquid-separation treatment in methyl t-butyl ether
  6. custompurified in a usual manner

Sources & evidence

ORD record
ord-7cc57d858b5b4a28b1f7ad20c50651ca
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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