Hydrochloric Acid → HCID 20232164, compound

HRID 1380315Notes

Reaction equation

HRID 1380315 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]([CH3:19])[NH:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1.[OH-].[Na+].[ClH:22]>O>[ClH:22].[NH:5]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]([CH3:19])[NH:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:10][CH:11]=1)[NH2:1]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-oneHCID 23668193Sodium Nitrite

Product 1

HCID 20232164HCID 20232164, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (3.6 g) in water (10 ml) was added dropwise to a solution of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (9.8 g), concentrated hydrochloric acid (10 ml) and water (30 ml) at 0° C. After stirring for 0.5 hours, a solution of stannous chloride dihydrate (43.12 g) in conc. hydrochloric acid (43 ml) was added thereto at 0° C. After stirring for 2 hours, the mixture was made alkaline with an aqueous solution of sodium hydroxide and the resultant precipitates were collected by filtration and washed with water. The crude product was dissolved in 10% hydrochloric acid under warming, and then allowed to stand at room temperature. The precipitates were collected by filtration and then dissolved in water. The aqueous solution was washed with ethyl acetate, treated with activated charcoal, and made alkaline with an aqueous solution of sodium hydroxide. The resultant precipitates were collected by filtration, washed with water, and recrystallized from 10% hydrochloric acid to give 6-(4-hydrazinophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one hydrochloride (3.2 g).

Workup

  1. customat 0° C
  2. stirringAfter stirring for 2 hours
  3. customthe resultant precipitates
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. dissolutionThe crude product was dissolved in 10% hydrochloric acid
  7. temperatureunder warming
  8. customto stand at room temperature
  9. filtrationThe precipitates were collected by filtration
  10. dissolutiondissolved in water
  11. washThe aqueous solution was washed with ethyl acetate
  12. additiontreated with activated charcoal
  13. customThe resultant precipitates
  14. filtrationwere collected by filtration
  15. washwashed with water
  16. customrecrystallized from 10% hydrochloric acid

Sources & evidence

ORD record
ord-77b92114b9d4420c8e6a33a42d3479c6
Source dataset
uspto-grants-1986_04
Patent number
US04581356

Reaction notes

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