Water → HCID 86736630, compound

HRID 1862815Notes

Reaction equation

HRID 1862815 reaction equation
[N:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[C:14]([O:16]CC)=[O:15])=[N+:2]=[N-:3].O>[OH-].[Na+]>[N:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[C:14]([OH:16])=[O:15])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 962WaterHCID 5178258Ethyl 4-azidoquinoline-3-carboxylate

Product 1

HCID 86736630HCID 86736630, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

4-Azido-3-carbethoxyquinoline (1.4 g; 0.006 M) was suspended in 10% aq. NaOH at ambient temperatures and the mixture stirred until complete solution had been obtained. The solution was filtered, cooled to 0° C. and acidified to pH 4 with 5 M HCl. The resulting precipitate was filtered, washed well with H2O and dried in vacuo over P2O5 to yield the product, 1.3 g (93%), as a monohydrate, m.p. 284° C. (dec.) (Found: N, 24.53%, C10H8N4O3 requires: N, 24.46%), νmax (nujol) 3200-3700(br), 2200-2600(br), 2110, 1700, 1492, 1327, 1215, 760cm-1, δ[(CD3)2SO] 7.45-3.1(m), 8.9(s) (aromatic protons). 14-16 (broad) (CO2H*+H2O),

Workup

  1. customhad been obtained
  2. filtrationThe solution was filtered
  3. filtrationThe resulting precipitate was filtered
  4. washwashed well with H2O
  5. dry with materialdried in vacuo over P2O5
  6. customto yield the product, 1.3 g (93%)

Sources & evidence

ORD record
ord-03a74a75be16457682cb359ce6f89ee0
Source dataset
uspto-grants-1979_09
Patent number
US04166817

Reaction notes

Loading…