Hydrochloric Acid → HCID 14423648, compound

HRID 1600741Notes

Reaction equation

HRID 1600741 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].Cl.O.O.[C:13](O)(=[O:17])[C:14](O)=[O:15].[OH-].[Na+]>>[CH3:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:2]=1[NH:1][C:13](=[O:17])[C:14](=[O:15])[NH:8]2

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 175932,3-DiaminotolueneHCID 61373Oxalic acid dihydrate

Product 1

HCID 14423648HCID 14423648, compoundYield 768.5%

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 2,3-diaminotoluene (0.498 g, 0.407 mmol, Aldrich) in 2N HCl (6 mL, 12 mmol), oxalic acid dihydrate (0.520 g, 0.412 mmol, Fisher) was added in one portion. The resulting deep purple solution was refluxed for 13 h, to give a purple suspension. This was cooled to 25° C., filtered, washed with water (5 mL), and dried in vacuo (0.1 mm Hg) to give a purple powder. This was taken up in 2N NaOH (25 mL, 50 mmol), giving a brown solution, which was filtered. The brown filtrate was acidified to pH 1.0 by addition of 2N HCl (25 mL, 50 mmol), resulting in a tan suspension. Filtration of the suspension and washing of the filter cake with water (5 mL) gave the title compound as a tan powder (551 mg, 64%); mp 325° C. (the block was preheated to 320° C.); 1H NMR (DMSO-d6) δ 2.26 (s, 3H), 6.86-7.01 (m, 3H), 11.6 (broad, 2H).

Workup

  1. temperatureThe resulting deep purple solution was refluxed for 13 h
  2. customto give a purple suspension
  3. filtrationfiltered
  4. washwashed with water (5 mL)
  5. customdried in vacuo (0.1 mm Hg)
  6. customto give a purple powder
  7. customgiving a brown solution, which
  8. filtrationwas filtered
  9. customresulting in a tan suspension
  10. filtrationFiltration of the suspension
  11. washwashing of the filter cake with water (5 mL)

Sources & evidence

ORD record
ord-edce5dbe4d5046ddb2f3edbea42ab5f4
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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