Sulfuric Acid → HCID 12378147, compound

HRID 1395278Notes

Reaction equation

HRID 1395278 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[C:9]([CH2:17][C:18](=O)[CH3:19])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S(=O)(=O)(O)O.[OH-].[Na+]>O.C(O)(=O)C>[NH2:8][C:4]1[N:3]=[C:2]2[C:7]([C:18]([CH3:19])=[CH:17][C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:1]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7166BenzoylacetoneHCID 88612,6-DiaminopyridineHCID 14798Sodium Hydroxide

Product 1

HCID 12378147HCID 12378147, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2,6-Diaminopyridine (16.4 g., 0.15 mole), 24 g. of benzoylacetone, 75 ml. of acetic acid and 1.5 ml of 96% sulfuric acid was refluxed with stirring for 24 hours. The solution was poured slowly with stirring into 50 g. of sodium hydroxide in 250 ml. of water; the temperature was held 20°-30° by cooling. The tan solid was filtered, washed well with water and dried, 21.8 g. One recrystallization from 100 ml. of 95% ethanol gave 6.9 g. of coarse needles, m.p. 65°-190°; a second recrystallization from 50 ml. of ethanol furnished 2.1 g. (6) of the title compound, m.p. 253°-255°; 1H nmr (deuteriochloroform+DMSO-d6, 60 MHz): δ2.67 (s,3H, CH3), 6.20 (broad exchangeable s, 2H, NH2), 6.92 (d, 1H, H5, J=9 Hz), 7.58 (d,1H, H6), 7.50 (m,3H,meta and para protons on C6H5), 8.30 (m,2H, ortho protons on C6H5).

Workup

  1. additionThe solution was poured slowly
  2. stirringwith stirring into 50 g
  3. customwas held 20°-30°
  4. temperatureby cooling
  5. filtrationThe tan solid was filtered
  6. washwashed well with water
  7. customdried
  8. customOne recrystallization from 100 ml
  9. customof 95% ethanol gave 6.9 g
  10. customa second recrystallization from 50 ml
  11. customof ethanol furnished 2.1 g

Sources & evidence

ORD record
ord-49de67da1b324fa1a5c80b532ea21161
Source dataset
uspto-grants-1980_05
Patent number
US04202981

Reaction notes

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