Hydrochloric Acid → 2-(Azidocarbonyl)-5-(benzyloxy)-4-oxo-1,4-dihydropyridine

HRID 1249601Notes

Reaction equation

HRID 1249601 reaction equation
Cl.[CH2:2]([O:9][C:10]1[C:11](=[O:20])[CH:12]=[C:13]([C:16]([NH:18][NH2:19])=[O:17])[NH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:21]([O-])=O.[Na+]>O>[N:18]([C:16]([C:13]1[NH:14][CH:15]=[C:10]([O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:11](=[O:20])[CH:12]=1)=[O:17])=[N+:19]=[N-:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 141824695-(Benzyloxy)-2-(hydrazinocarbonyl)-4-oxo-1,4-dihydropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 202236492-(Azidocarbonyl)-5-(benzyloxy)-4-oxo-1,4-dihydropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of concentrated hydrochloric acid (3 ml) in water (10 ml) was cooled to 0° C. and treated with 5-(benzyloxy)-2-(hydrazinocarbonyl)-4-oxo-1,4-dihydropyridine (3 g, 11.58 mmole) to form a thick paste. A solution of sodium nitrite (1.68 g, 23.17 mmole) in water (30 ml) was added in 2 ml portions with mechanical swirling of the reaction vessel. The resulting mixture was stirred for 3.5 hours and filtered. The resulting pasty solid was washed with water, ice-cold ethanol, ether and hexane. After drying thoroughly under high vacuum, the yield of the title compound was 2.6 g.

Workup

  1. customto form a thick paste
  2. filtrationfiltered
  3. washThe resulting pasty solid was washed with water, ice-cold ethanol, ether and hexane
  4. customAfter drying thoroughly under high vacuum

Sources & evidence

ORD record
ord-7eb2d94a876e42cfb8551bf0713ab766
Source dataset
uspto-grants-1986_12
Patent number
US04632985

Reaction notes

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