Phosphorus oxychloride → Ethyl 4-chloroquinoline-2-carboxylate

HRID 1948297Notes

Reaction equation

HRID 1948297 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=1>>[Cl:3][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469285HCID 178469285, compound

Product 1

HCID 269156Ethyl 4-chloroquinoline-2-carboxylate

Procedure

Phosphorous oxychloride (5 ml) was added to ethyl 4-hydroxyquinoline-2-carboxylate (1.01 g). The reaction mixture was subjected to single-mode microwave at 100° C. for 30 min using a Smith Microwave Synthesizer. The solvent was removed in vacuo and recrystallized with acetone to gave the title compound as a white solid (1.90 g). MS (ES) MH+: 235, 237 for C12H10ClNO2; NMR (CDCl3): 1.44 (t, 3H, J=7.16), 4.51 (q, 2H, J=7.16), 7.19 (s, 1H), 7.71 (m, 1H), 7.81 (m, 1H), 8.22 (m, 1H), 8.36 (d, 1H, J=8.29).

Workup

  1. customat 100° C.
  2. customfor 30 min
  3. customThe solvent was removed in vacuo
  4. customrecrystallized with acetone

Sources & evidence

ORD record
ord-8cbf290327a44490a993287822b2b8bc
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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