Sodium Azide → HCID 20393614, compound

HRID 1862818Notes

Reaction equation

HRID 1862818 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[C:11]([CH3:17])[N:10]=2)([O:3][CH2:4][CH3:5])=[O:2].[N-:18]=[N+:19]=[N-:20].[Na+]>O>[N:18]([C:15]1[C:14]2[C:9](=[N:10][C:11]([CH3:17])=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:1]([O:3][CH2:4][CH3:5])=[O:2])=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 10562672Ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylate

Product 1

HCID 20393614HCID 20393614, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Carbethoxy-4-chloro-7-methyl-1,8-naphthyridine (0.8 g; 0.03 M) was dissolved in dry D.M.F. (5 ml) at ambient temperatures and NaN3 (0.5 g; 0.007 M) added. This mixture was stirred for 20 hr. at ambient temperatures and then poured into a large volume (1 l) of H2O. The product (0.64 g; 83%), m.p. 114°-115° C. (dec.), was filtered off, washed with H2O and dried over P2O5 in vacuo (Found: N, 27.49; C, 55.59; H, 4.50%. C12H11N5O2 requires: N, 27.24; C, 56.03; H, 4.28%), νmax (KBr) 3080, 2900, 2142, 1708, 1600, 1550, 1472, 1375, 1268, 1210, 1194, 1050, 1038, 806 cm-1, δ [(CD3)2SO] 1.38 (t), 4.40 (q), (CH3CH2), 2.68 (s), (CH3), 7.5 (d), 8.5 (d), 9.14 (s) (heterocyclic protons), m/e 257 (M+ ; 65%) 229 (M+ --N2 ; 32%), 212 (M+ --OC2H5 ; 15%), 201 (52%), 133 (100%).

Workup

  1. filtrationThe product (0.64 g; 83%), m.p. 114°-115° C. (dec.), was filtered off
  2. washwashed with H2O
  3. dry with materialdried over P2O5 in vacuo (Found: N, 27.49; C, 55.59; H, 4.50%. C12H11N5O2 requires: N, 27.24; C, 56.03; H, 4.28%), νmax (KBr) 3080, 2900, 2142, 1708, 1600, 1550, 1472, 1375, 1268, 1210, 1194, 1050, 1038, 806 cm-1, δ [(CD3)2SO] 1.38 (t), 4.40 (q), (CH3CH2), 2.68 (s), (CH3), 7.5 (d), 8.5 (d), 9.14 (s) (heterocyclic protons), m/e 257 (M+ ; 65%) 229 (M+ --N2 ; 32%), 212 (M+ --OC2H5 ; 15%), 201 (52%), 133 (100%)

Sources & evidence

ORD record
ord-de975dadef5a4ff4a8eeaa0f3022c277
Source dataset
uspto-grants-1979_09
Patent number
US04166817

Reaction notes

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