Acetic Acid → 2-Methyl-4-methoxyaniline

HRID 1732164Notes

Reaction equation

HRID 1732164 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-])=O.[C:11](O)(=[O:13])C>O>[NH2:1][C:4]1[C:5]([CH3:10])=[CH:6][CH:7]=[CH:8][CH:9]=1.[CH3:10][C:5]1[CH:6]=[C:7]([O:13][CH3:11])[CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69442-Nitrotoluene

Product 2

HCID 7242O-ToluidineHCID 76102-Methyl-4-methoxyanilineYield 76.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The same catalytic reduction reaction as in Example 1 was carried out except that o-nitrotoluene was used in an amount of 68.6 g (0.5 mole), and 68.6 g of glacial acetic acid was used instead of distilled water. The reaction required a period of 220 minutes with the absorption of 26.4 liters of hydrogen until its termination. The reaction solution was worked up in the same way as in Example 1 to give 9.0 g of o-toluidine and 53.1 g (yield 76.6%) of 2-methyl-4-methoxyaniline. The 2-methyl-4-methoxyaniline was found to have a purity of 99.0% by gas chromatography.

Workup

  1. customThe same catalytic reduction reaction as in Example 1
  2. customThe reaction
  3. customrequired a period of 220 minutes with the absorption of 26.4 liters of hydrogen until its termination

Sources & evidence

ORD record
ord-5017d5abd00e4ef69a263fe04aed2aec
Source dataset
uspto-grants-1986_11
Patent number
US04625062

Reaction notes

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