Acetic Anhydride → 1-(5-(Benzyloxy)-1H-indazol-1-yl)ethan-1-one

HRID 1726045Notes

Reaction equation

HRID 1726045 reaction equation
[C:1]([O:4]C(=O)C)(=O)[CH3:2].[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([CH3:23])[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:24](OC(C)(C)C)=O>C1(C)C=CC=CC=1>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:19](=[CH:20][CH:21]=1)[N:22]([C:1](=[O:4])[CH3:2])[N:24]=[CH:23]2)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10906Tert-Butyl nitriteHCID 167730534-(Benzyloxy)-2-methylaniline

Product 1

HCID 225672491-(5-(Benzyloxy)-1H-indazol-1-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

10.5 ml of acetic anhydride are run into a solution of 7.14 g of 4-benzyloxy-2-methylphenylamine in 26 ml of toluene. The medium is heated to around 90° C. and 9.28 ml of tert-butyl nitrite are run in to the solution, dropwise. The reaction medium is heated at around 90° C. for two hours. The reaction crude is concentrated to dryness in a rotary evaporator. The solid is taken up in ethyl acetate and then filtered and rinsed with isopropyl ether. 3.41 g of 1-(5-benzyloxyindazol-1-yl)ethanone are collected.

Workup

  1. temperatureThe reaction medium is heated at around 90° C. for two hours
  2. customThe reaction crude
  3. concentrationis concentrated to dryness in a rotary evaporator
  4. filtrationfiltered
  5. washrinsed with isopropyl ether
  6. custom3.41 g of 1-(5-benzyloxyindazol-1-yl)ethanone are collected

Sources & evidence

ORD record
ord-eea8bbcbface4f2ba20769c71c96cbbb
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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