4-Methyl-3-nitroaniline → tert-Butyl (4-methyl-3-nitrophenyl)carbamate

HRID 1465027Notes

Reaction equation

HRID 1465027 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12](=O)([OH:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]>C1COCC1>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 83904-Methyl-3-nitroanilineHCID 3015642Mono-tert-butyl carbonate

Product 1

HCID 18954623tert-Butyl (4-methyl-3-nitrophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

4-Methyl-3-nitroaniline (5.0 g, 32.86 mmol) was dissolved in anhydrous THF (25 mL). t-Butyl bicarbonate (7.5 mL, 32.86 mmol) dissolved in anhydrous THF (25 mL) was added slowly to the reaction mixture, which was stirred at 65° C. for 18 hours. After the reaction was completed the remaining organic solvent was distilled under reduced pressure, and water was added thereto. The resulting yellow solid was filtered and dried to obtain the title compound without further purification.

Workup

  1. additionwas added slowly to the reaction mixture, which
  2. distillationwas distilled under reduced pressure, and water
  3. additionwas added
  4. filtrationThe resulting yellow solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-d547698dd7ee4a56bca561fee49ee039
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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