Triethylamine → 6-(1-cyclopropanecarbonyl-1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 1380320Notes

Reaction equation

HRID 1380320 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[NH:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]([CH3:24])[NH:19][C:20](=[O:23])[NH:21][N:22]=3)=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C>CN(C)C=O>[CH:1]1([C:4]([N:7]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[CH:18]([CH3:24])[NH:19][C:20](=[O:23])[NH:21][N:22]=4)=[CH:14][CH:15]=3)[CH2:10][CH2:9][CH2:8]2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 23326481HCID 23326481, compound

Product 1

HCID 233264396-(1-cyclopropanecarbonyl-1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-oneYield 27.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopropanecarbonyl chloride (0.47 g) was added dropwise to a stirred solution of 6-(1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.73 g) and triethylamine (0.6 g) in N,N-dimethylformamide (7.3 ml) under ice cooling and the stirring was continued for 30 minutes. The solution was evaporated in vacuo and the residue was dissolved in chloroform. The solution was washed with diluted hydrochloric acid, dried, and evaporated. The residue was chromatographed on silica gel (5 g) using chloroform and then a mixture of chloroform and methanol (20:1) as an eluents. The eluates were evaporated in vacuo and the oily residue was crystallized from ethanol to give 6-(1-cyclopropanecarbonyl-1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.26 g).

Workup

  1. customThe solution was evaporated in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe solution was washed with diluted hydrochloric acid
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (5 g)
  7. additiona mixture of chloroform and methanol (20:1) as an eluents
  8. customThe eluates were evaporated in vacuo
  9. customthe oily residue was crystallized from ethanol

Sources & evidence

ORD record
ord-db557d87ad344cec89a3d2802a92fd15
Source dataset
uspto-grants-1986_04
Patent number
US04581356

Reaction notes

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