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

HRID 66705
Notes
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Reaction equation

HRID 66705 reaction equation
C(#N)C1C=CC=C(C#[N:6])C=1.[C]=O.[H][H].[NH3:15].[C:16]1([CH3:23])[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1>[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>[C:16]1([CH3:23])[C:17]([NH2:6])=[C:18]([CH3:22])[C:19]([NH2:15])=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 222AmmoniaHCID 7929M-Xylene3×HCID 12276Isophthalonitrile3×HCID 178418361HCID 178418361, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 46255812,4-Dimethylbenzene-1,3-diamineYield 96.4%

Reagents, catalysts & solvents 1

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)Catalyst

Conditions

Temperature
160 °C

Procedure

0.76 g of dicobalt octacarbonyl, 1 g of isophthalonitrile and 20 ml of m-xylene were charged into a 100 ml eggplant type flask equipped with a reflux condenser and a gas inlet tube and the air in the flask was thoroughly replaced while introducing carbon monoxide through the gas inlet tube. Thereafter, the flask was heated in an oil bath at 160° C. for 90 minutes under reflux while passing carbon monoxide therethrough. After the heating, the flask was cooled to room temperature and the resulting precipitate was directly transferred into a 100 ml shaking type autoclave together with solvent m-xylene. After adding 9 g of isophthalonitrile and 10 ml of m-xylene thereto, the gas in the autoclave was replaced with hydrogen. Further 10 ml of liquid ammonia was added thereto and the isophthalonitrile was hydrogenated at a reaction temperature of 100° C. under an initially charged hydrogen pressure of 260 kg/cm2 gage. The reaction was completed in 120 minutes and m-xylenediamine was obtained in a yield of 96.4%.

Workup

  1. customequipped with a reflux condenser and a gas inlet tube
  2. temperatureunder reflux
  3. temperatureAfter the heating, the flask was cooled to room temperature
  4. customwas hydrogenated at a reaction temperature of 100° C. under an initially charged hydrogen

Sources & evidence

ORD record
ord-d8fb09eaf9d945478b893dfc703920c6
Source dataset
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04343722

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes