Acetic Acid → HCID 178448822, compound

HRID 1834370Notes

Reaction equation

HRID 1834370 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:9]([NH2:16])[C:8]([NH2:17])=[N:7][C:6]=1[CH3:18])[CH3:2].C(O)(=O)C.[N:24]([O-])=O.[Na+]>O>[CH2:1]([O:3][C:4]([C:5]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:9]2[N:16]=[N:24][NH:17][C:8]2=[N:7][C:6]=1[CH3:18])=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 123876125,6-Diamino-4-butylamino-2-methylnicotinic acid ethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 178448822HCID 178448822, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.66 g. of 5,6-diamino-4-butylamino-2-methylnicotinic acid ethyl ester (0.01 mol.) are dissolved in 20 ml. of acetic acid and 5 ml. of water. The mixture is cooled to 5° with stirring. At this temperature, a solution of 0.9 g. of sodium nitrite in 5 ml. of water is showly added dropwise. Stirring is continued for an additional 8 hours. The solvent is distilled off and the residue treated with 20 ml. of water and extracted three times with 10 ml. portions of chloroform. The organic layers are dried with sodium sulfate, filtered and evaporated. The crystalline 7-butylamino-5-methyl-3H-[1,2,3]-triazolo-[4,5-b]pyridine-6-carboxylic acid ethyl ester remains and is recrystallized from methanol, yield 2.3 g. (83%), m.p. 188°-189°.

Workup

  1. temperatureThe mixture is cooled to 5°
  2. stirringStirring
  3. distillationThe solvent is distilled off
  4. additionthe residue treated with 20 ml
  5. extractionof water and extracted three times with 10 ml
  6. dry with materialThe organic layers are dried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customis recrystallized from methanol, yield 2.3 g

Sources & evidence

ORD record
ord-8d312283e22b4c25bd71946b749dbc9d
Source dataset
uspto-grants-1978_01
Patent number
US04070362

Reaction notes

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