Ethylamine → N-(2-Chloro-4-methyl-3-pyridinyl)-2-ethylamino-3-pyridinecarboxamide

HRID 2380234Notes

Reaction equation

HRID 2380234 reaction equation
[CH2:1]([NH2:3])[CH3:2].Cl[C:5]1[C:10]([C:11]([NH:13][C:14]2[C:15]([Cl:21])=[N:16][CH:17]=[CH:18][C:19]=2[CH3:20])=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1.CCCCCC>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[Cl:21][C:15]1[C:14]([NH:13][C:11]([C:10]2[C:5]([NH:3][CH2:1][CH3:2])=[N:6][CH:7]=[CH:8][CH:9]=2)=[O:12])=[C:19]([CH3:20])[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 6341EthylamineHCID 8058HexaneHCID 104238682-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

Product 1

HCID 11066217N-(2-Chloro-4-methyl-3-pyridinyl)-2-ethylamino-3-pyridinecarboxamideYield 76.2%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
165 °C

Procedure

Ethylamine (12.7 g) was added to a suspension of 21.0 g of the 2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide in 150 ml of xylene in a steel bomb. The mixture was then heated in an oil bath to 165° C. for 6 hrs. and then stirred overnight at room temperature. The solvent was removed in vacuo and water added to the residue. The product was extracted with ether, dried (sodium sulfate) and concentrated to give an oil. This was dissolved in ethyl acetate followed by hexane at which time a precipitate formed. The solid was filtered and dried to give 16.5 g of the title compound, m.p. 122°-124° C.

Workup

  1. customThe solvent was removed in vacuo and water
  2. additionadded to the residue
  3. extractionThe product was extracted with ether
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customto give an oil
  7. customformed
  8. filtrationThe solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-144febdc754f426cbcf0984c8277fb02
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

Loading…