Ethyl 2-oxocyclohexanecarboxylate → HCID 14423598, compound

HRID 1199614Notes

Reaction equation

HRID 1199614 reaction equation
[F:1][C:2]1[C:19]([NH:20][NH2:21])=[CH:18][C:5]2[N:6]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.C([O:24][C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C:28]1=O)=O)C.[O-]CC.[Na+]>C(O)C>[F:1][C:2]1[C:19]([N:20]2[C:25](=[O:24])[CH:27]3[C:28]([CH2:29][CH2:30][CH2:31][CH2:32]3)=[N:21]2)=[CH:18][C:5]2[N:6]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 2723922Sodium ethoxideHCID 14423585HCID 14423585, compound

Product 1

HCID 14423598HCID 14423598, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-fluoro-6-hydrazino-4-(pyridin-2-ylmethyl)-2H-1,4-benzoxazin-3(4H)-one (1.49 g), 2-ethoxycarbonyl-cyclohexanone (0.9 g) and ethanol (20 ml) was admixed with a catalytic amount of sodium ethoxide, and heated under reflux for 5 hours. The reaction mixture was distilled to remove the ethanol therefrom, admixed with toluene (30 ml), heated under reflux for 10 minutes, cooled to a temperature of 0° to 10° C., and filtered. The solid portion thus obtained was washed with n-hexane, and dried, so that the aimed compound, i.e. 7-fluoro-6-(3,3a,4,5,6,7-hexahydro-2H-indazole-3-on-2-yl)-4-(pyridin-2-ylmethyl)-2H-1,4-benzoxazin-3(4H)-one (1.24 g) was obtained. m.p. 216°-219° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. distillationThe reaction mixture was distilled
  4. customto remove the ethanol
  5. temperatureheated
  6. temperatureunder reflux for 10 minutes
  7. temperaturecooled to a temperature of 0° to 10° C.
  8. filtrationfiltered
  9. customThe solid portion thus obtained
  10. washwas washed with n-hexane
  11. dry with materialdried, so that the aimed compound

Sources & evidence

ORD record
ord-e4a0f208c709484a9a3db4285ac63a4d
Source dataset
uspto-grants-1990_02
Patent number
US04902335

Reaction notes

Loading…