HCID 20393614, compound → HCID 20393620, compound

HRID 1862819Notes

Reaction equation

HRID 1862819 reaction equation
[N:1]([C:4]1[C:13]2[C:8](=[N:9][C:10]([CH3:14])=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[C:15]([O:17]CC)=[O:16])=[N+:2]=[N-:3]>[OH-].[Na+]>[N:1]([C:4]1[C:13]2[C:8](=[N:9][C:10]([CH3:14])=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[C:15]([OH:17])=[O:16])=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 20393614HCID 20393614, compound

Product 1

HCID 20393620HCID 20393620, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4-Azido-3-carbethoxy-7-methyl-1,8-naphthyridine (2.4 g; 0.008 M) was suspended in 10% aq. NaOH (60 ml) and the mixture stirred at ambient temperatures until all the ester had reacted. The insoluble material was removed by filtration and redissolved in H2O. The pH of the solution was adjusted to 3.5 with 5 M HCl and the resulting precipitate (1.3 g; 71%) filtered off, washed with H2O and dried over P2O5 in vacuo, m.p. 198° C. (explosive dec. on rapid heating), (Found: N, 29.66%; C10H7N5O2.1/2H2O requires N, 29.41%), m/e 201 (M+--N2 ; 95%), 159 (100%) νmax (KBr) 3430 (br), 2430 (br), 2150, 2060-1800 (br), 1705, 1605, 1560, 1475, 1375, 1260, 1230, 1202, 920, 810 cm-1, δ [(CD3)2SO] 2.72 (s) (CH3), 7.62 (d), 8.62 (d), 9.29 (s) (heterocyclic protons), CO2H* diffuse low-field resonance, *exchangeable with D2O.

Workup

  1. customhad reacted
  2. customThe insoluble material was removed by filtration
  3. dissolutionredissolved in H2O
  4. filtrationthe resulting precipitate (1.3 g; 71%) filtered off
  5. washwashed with H2O
  6. dry with materialdried over P2O5 in vacuo, m.p. 198° C. (explosive dec. on rapid heating), (Found: N, 29.66%; C10H7N5O2.1/2H2O requires N, 29.41%), m/e 201 (M+--N2 ; 95%), 159 (100%) νmax (KBr) 3430 (br), 2430 (br), 2150, 2060-1800 (br), 1705, 1605, 1560, 1475, 1375, 1260, 1230, 1202, 920, 810 cm-1, δ [(CD3)2SO] 2.72 (s) (CH3), 7.62 (d), 8.62 (d), 9.29 (s) (heterocyclic protons), CO2H

Sources & evidence

ORD record
ord-07d05a463f404496a348f58bb890471a
Source dataset
uspto-grants-1979_09
Patent number
US04166817

Reaction notes

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