Sodium Carbonate → HCID 13019470, compound

HRID 2285731Notes

Reaction equation

HRID 2285731 reaction equation
[N:1]([O-])=O.[Na+].[CH3:5][N:6]([CH2:8][CH2:9][CH:10]([C:16]1[CH:25]=[CH:24][C:19](C(NN)=O)=[CH:18][CH:17]=1)[C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:7].C(=O)([O-])[O-].[Na+].[Na+]>O.Cl>[NH2:1][C:19]1[CH:24]=[CH:25][C:16]([CH:10]([C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)[CH2:9][CH2:8][N:6]([CH3:7])[CH3:5])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 13019469HCID 13019469, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13019470HCID 13019470, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (0.5 g) in water (5 ml) was added dropwise to a stirred solution of 4-[3-(N,N-dimethylamino)-1-(imidazol-2-yl)propyl]benzoic acid hydrazide (2.0 g) in 2 N hydrochloric acid (10.5 ml) and water (50 ml) at 0° to 5° C. After 30 min. the solution was basified by adding 2 N sodium carbonate (15 ml) and then extracted with ether (3×50 ml). The extracts were dried (Na2SO4) and concentrated to an off white solid (1.7 g). This solid was dissolved in toluene (40 ml) and benzyl alcohol (1.5 ml) and heated on a steam bath for 2 h. Solvent was removed and the residue taken up in ethanol (20 ml) and hydrogenated at atmospheric pressure over 10% palladium oxide on charcoal (0.5 g) for 3 h. The catalyst was filtered off and the filtrate treated with a solution of maleic acid (1.8 g) in ethanol (10 ml). Removal of the solvent and trituration of the residue with dry ether afforded a white solid. Recrystallisation from ethanolether gave the trimaleate salt of the title compound, m.p. 132°-133° (2.6 g).

Workup

  1. extractionextracted with ether (3×50 ml)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. concentrationconcentrated to an off white solid (1.7 g)
  4. dissolutionThis solid was dissolved in toluene (40 ml)
  5. temperaturebenzyl alcohol (1.5 ml) and heated on a steam bath for 2 h
  6. customSolvent was removed
  7. waitthe residue taken up in ethanol (20 ml) and hydrogenated at atmospheric pressure over 10% palladium oxide on charcoal (0.5 g) for 3 h
  8. filtrationThe catalyst was filtered off
  9. additionthe filtrate treated with a solution of maleic acid (1.8 g) in ethanol (10 ml)
  10. customRemoval of the solvent and trituration of the residue with dry ether
  11. customafforded a white solid
  12. customRecrystallisation from ethanolether

Sources & evidence

ORD record
ord-0bbbc5715d954c8083e0ff99d7d7367f
Source dataset
uspto-grants-1982_04
Patent number
US04324792

Reaction notes

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