N-(4-(1,1-Dimethylethyl)-2-nitrophenyl)acetamide → 4-tert-Butyl-2-nitroaniline

HRID 1424238Notes

Reaction equation

HRID 1424238 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11]C(=O)C)=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 97069N-(4-(1,1-Dimethylethyl)-2-nitrophenyl)acetamideHCID 10942334Sodium Methoxide

Product 1

HCID 805734-tert-Butyl-2-nitroanilineYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A reactor was charged with methanol (13.5 L) and N-(4-tert-butyl-2-nitrophenyl) acetamide (Preparation 109, 7.0 kg, 29.6 mol). The mixture was stirred for ten minutes then a solution of 30% sodium methoxide in methanol (6.49 L, 35.5 mol) was added slowly at room temperature. The mixture was heated slowly to reflux and held at that temperature for two hours. The methanol was distilled to dryness under vacuum at 50-55° C. and the solids cooled to room temperature. The residue was stirred in water (35 L) for one hour and the solids collected by filtration, washed with water (14 L), and dried at 45-50° C. to provide 5.3 kg of the title compound.

Workup

  1. temperatureThe mixture was heated slowly
  2. temperatureto reflux
  3. distillationThe methanol was distilled to dryness under vacuum at 50-55° C.
  4. stirringThe residue was stirred in water (35 L) for one hour
  5. filtrationthe solids collected by filtration
  6. washwashed with water (14 L)
  7. customdried at 45-50° C.

Sources & evidence

ORD record
ord-70ac5d8abdff47fbba3a9a54bb34319b
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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