Ethyl 4-azido-7-chloroquinoline-3-carboxylate → 4-Azido-7-chloroquinoline-3-carboxylic acid

HRID 1862821Notes

Reaction equation

HRID 1862821 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[N:16]=[N+:17]=[N-:18])=[CH:13][CH:12]=[C:11]([Cl:19])[CH:10]=2)=[O:5])C>[OH-].[Na+]>[N:16]([C:15]1[C:14]2[C:9](=[CH:10][C:11]([Cl:19])=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3])=[N+:17]=[N-:18]

Participants

3

Reactant 1

HCID 3690236Ethyl 4-azido-7-chloroquinoline-3-carboxylate

Product 1

HCID 203936224-Azido-7-chloroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl-4-azido-7-chloroquinoline-3-carboxylate (0.57 g; 0.002 M) in 10% aq. NaOH (10 ml) and stirred at 40° C. for 5 hr. The unreacted ester, m.p. 91°-4° C., was filtered off, the filtrate acidified to pH 3 with 5 M HCl, the product filtered off, washed well with water and dried in vacuo over P2O5. 0.33 g (66%), m.p. 284°-6° C. (dec.), (Found: C, 46.7; H, 2.3; Cl 14.1%. C10H5ClN4O2.1/2H2O requires C, 46.6; H, 2.4; Cl 13.8%), νmax (KBr) 2158, 1705 (br), 1608, 1562, 1395 (br), 1210 and 798 cm-1, δ [(CD3)2SO] 7.72 (m), 8.09 (d), 8.36 (d) and 9.18 (s) (aromatic H's)

Workup

  1. filtrationThe unreacted ester, m.p. 91°-4° C., was filtered off
  2. filtrationthe product filtered off
  3. washwashed well with water
  4. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-ee60d5db8a8c4694a53e7bee77fab355
Source dataset
uspto-grants-1979_09
Patent number
US04166817

Reaction notes

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