Ethanol → 3,4-Dimethylbenzene-1,2-diamine

HRID 922091Notes

Reaction equation

HRID 922091 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-])=O)[C:3]=1[NH2:4].C(O)C.[OH-].[Na+]>O.[Zn]>[CH3:1][C:2]1[C:3]([NH2:4])=[C:5]([NH2:10])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 5971662,3-Dimethyl-6-nitroaniline

Product 1

HCID 5210773,4-Dimethylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

To a 125 mL round bottom flask 2.20 g of 2,3-dimethyl-6-nitro-aniline (13.2 mmol) was added. Then 15 mL of ethanol was added to the flask followed by the addition of 4 mL of 20 wt % NaOH in water. Then 2.0 g of zinc dust was added to the flask. The flask was fitted with a condenser and was left to reflux with stirring. After about 0.5 hours the mixture became very pale-brown. After refluxing for 18 hours the mixture was filtered hot to give a pale filtrate which quickly became dark red. C8H12N2, fw=136.19. Yield 1.78 g, 98.7%. Mp: 60° C. (melt). 1H NMR (300 MHz, CDCl3): δ 6.54 (s, 2H), 3.46 (br s, 2H), 3.21 (br s, 2H), 2.22 (s, 3H), 2.11 (s, 3H). Rf=0.68 (ethyl acetate/silica).

Workup

  1. customThe flask was fitted with a condenser
  2. waitwas left
  3. temperatureto reflux
  4. temperatureAfter refluxing for 18 hours the mixture
  5. filtrationwas filtered hot
  6. customto give a pale filtrate which quickly became dark red

Sources & evidence

ORD record
ord-7d22299a05364aa2ae666609107d500b
Source dataset
uspto-grants-2016_03
Patent number
US09278894B2

Reaction notes

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