Tert-Butylamine → HCID 90308803, compound

HRID 2283721Notes

Reaction equation

HRID 2283721 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[N+:6]([C:9]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:10]=1[CH:11]=O)([O-])=O>C(O)C>[C:1]([N:5]1[CH:11]=[C:10]2[C:9]([CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 682502,4-Dinitrobenzaldehyde

Product 1

HCID 90308803HCID 90308803, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Tert-butylamine (2 mL) was added to a solution of 2,4-dinitrobenzaldehyde (1.96 g) in ethanol (10 mL), and the reaction solution was stirred at 40° C. for 30 minutes. The solvent was evaporated under vacuum, then tert-butylamine (1 mL) was added to the resultant residue, and the reaction solution was heated at 50° C. for 30 minutes. The solvent was evaporated under vacuum, then trimethyl phosphite (6 mL) was added, and the reaction solution was stirred at 110° C. for 1 hour. The solvent was evaporated under vacuum, and the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate). Thereafter, isopropyl ether was added to the resultant residue, and the precipitate was filtrated to obtain 2-(tert-butyl)-6-nitro-2H-indazole as a white solid.

Workup

  1. customThe solvent was evaporated under vacuum
  2. additiontert-butylamine (1 mL) was added to the resultant residue
  3. temperaturethe reaction solution was heated at 50° C. for 30 minutes
  4. customThe solvent was evaporated under vacuum
  5. additiontrimethyl phosphite (6 mL) was added
  6. stirringthe reaction solution was stirred at 110° C. for 1 hour
  7. customThe solvent was evaporated under vacuum
  8. customthe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)
  9. additionThereafter, isopropyl ether was added to the resultant residue
  10. filtrationthe precipitate was filtrated

Sources & evidence

ORD record
ord-77cb99a00e354aa4b8da0b88d2f8dd83
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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