Acetic Anhydride → 1-(6-nitroindazol-1-yl)ethanone

HRID 1750886Notes

Reaction equation

HRID 1750886 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:20][C:21](OC(C)=O)=[O:22].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O.O>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[C:21](=[O:22])[CH3:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 242396-NitroindazoleHCID 2855718-Crown-6

Product 1

HCID 3081141-(6-nitroindazol-1-yl)ethanoneYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-nitroindazole (1 g, 6.13 mmol) was dissolved in dimethylformamide (15 mL), and added with triethylamine (1.7 mL, 12.2 mmol), Ac2O (0.69 mL, 7.4 mmol) and 18-Crown-6 (0.38 g, 1.23 mmol). The reaction solution was stirred for about 4 hours at room temperature. The reaction mixture was added with distilled water, and further stirred for about 1 hour. The resulting solid was filtered under reduced pressure, and washed with distilled water. The filtered solid was dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (0.9 g, 75%).

Workup

  1. stirringfurther stirred for about 1 hour
  2. filtrationThe resulting solid was filtered under reduced pressure
  3. washwashed with distilled water
  4. customThe filtered solid was dried
  5. temperaturewith warm wind in an oven (40° C.) for 3 hours or more

Sources & evidence

ORD record
ord-ac598785c0754aaa99379553c6584f10
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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