Acetic Acid → 2-Chloro-4-methoxyaniline

HRID 1732165Notes

Reaction equation

HRID 1732165 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11](O)(=[O:13])C>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[Cl:1][C:2]1[CH:7]=[C:6]([O:13][CH3:11])[CH:5]=[CH:4][C:3]=1[NH2:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69451-Chloro-2-nitrobenzene

Product 2

HCID 72402-ChloroanilineHCID 4074322-Chloro-4-methoxyanilineYield 65.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The same catalytic reduction reaction as in Example 1 was carried out except that 157.6 g (1.0 mole) of o-chloronitrobenzene was used instead of 137.1 g (1.0 mole) of o-nitrotoluene and a 50% aqueous solution of acetic acid was used instead of distilled water. The reaction required a period of 480 minutes with the absorption of 53.0 liters of hydrogen until its termination. Subsequently, the reaction solution was worked up in the same way as in Example 1 to give 8.5 g of o-chloroaniline as an initial distillate and 103.7 g (yield 65.5%) of 2-chloro-4-methoxyaniline (boiling point 141° to 143° C./20 mmHg) as a main distillate. The main distillate was found to have a purity of 99.5% by gas chromatography.

Workup

  1. customThe same catalytic reduction reaction as in Example 1
  2. customThe reaction
  3. customrequired a period of 480 minutes with the absorption of 53.0 liters of hydrogen until its termination

Sources & evidence

ORD record
ord-e64cbb4d38124f5cb9ceed46954b288e
Source dataset
uspto-grants-1986_11
Patent number
US04625062

Reaction notes

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