5-(Methylthio)-2-nitroaniline → HCID 20393009, compound

HRID 1160168

Reaction equation

HRID 1160168 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-])=O)=[C:7]([CH:9]=1)[NH2:8]>C(O)(=O)C.[Zn]>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:10])=[C:7]([NH2:8])[CH:9]=1

Participants

4

Reactant 1

HCID 105354825-(Methylthio)-2-nitroaniline

Product 1

HCID 20393009HCID 20393009, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 5-methylthio-2-nitroaniline (50 mg; 0.27 mmol) in acetic acid (2 ml) was heated to 85° C. Zinc powder (71 mg; 1.09 mmol) was then added portionwise over 15 minutes and the resulting solution was maintained at 85° C. for 2 hours. The hot reaction mixture was then filtered through celite and the filter cake washed with hot acetic acid (10 ml). The filtrate was evaporated to dryness to give crude 4-methylthio-1,2-phenylenediamine (42 mg, 100%). This was used directly in the next step without purification.

Workup

  1. filtrationThe hot reaction mixture was then filtered through celite
  2. washthe filter cake washed with hot acetic acid (10 ml)
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-680012fb0c2e4520b00d0e1c4239d0ee
Source dataset
uspto-grants-2010_10
Patent number
US07816369B2

Linked notes

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