Acetone → HCID 14708756, compound

HRID 358737Notes

Reaction equation

HRID 358737 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N-:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na+].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.CC(C)=O.C(OCC)(=O)C>[Cl-].[Na+].O.CCCCCC>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 8857Ethyl Acetate2×HCID 256687Methyl 4-(bromomethyl)benzoateHCID 14434205HCID 14434205, compound

Product 1

HCID 14708756HCID 14708756, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 3.7 g. sodium 6-nitroindazolide, 4.58 g. of methyl 4-bromomethylbenzoate (F) and 120 ml. acetone was heated under reflux in a nitrogen atmosphere for 54 hours and then diluted with 250 ml. ethyl acetate and 40 ml. of 50% w/v brine. The organic layer was separated, washed with brine, dried (MgSO4), and evaporated to give a brown solid. Early fractions from chromatography of the solid on a Waters 500 HPLC (SiO2, 25% v/v ethyl acetate in hexane) yielded a solid which was crystallized from ethyl acetate to give methyl 4-(6-nitroindazol-1-yl)methylbenzoate (J) as light yellow needles, 1.71 g. (28%); m.p. 171°-172.5° C.; partial 13C-NMR: 134.10 (C-3).

Workup

  1. additionA mixture of 3.7 g
  2. temperatureunder reflux in a nitrogen atmosphere for 54 hours
  3. additiondiluted with 250 ml
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a brown solid
  9. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-fee647d56fb64b0d8cc255d285d2b5c4
Source dataset
uspto-grants-1991_03
Patent number
US04997844

Reaction notes

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