Hydrochloric Acid → HCID 14423648, compound

HRID 1857415Notes

Reaction equation

HRID 1857415 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 2 N 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 2 N NaOH (25 mL, 50 mmol), giving a brown solution, which was filtered. The brown filtrate was acidified to pH 1.0 by addition of 2 N 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, 3 H), 11.6 (broad, 2 H).

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-ef8172fa08eb4c56be13f8e02a3627c1
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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