Phosphorus oxychloride → ethyl 4-chloro-6-ethoxyquinoline-3-carboxylate

HRID 2169845Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]2O)[CH3:2].O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)[N:10]=[CH:9][C:8]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178469590HCID 178469590, compound

Product 1

HCID 727468ethyl 4-chloro-6-ethoxyquinoline-3-carboxylate

Procedure

Prepared as in Example 1b from ethyl 6-ethoxy-4-hydroxyquinoline-3-carboxylate (Example 13c) and POCl3 as pale yellow solid (100%). 1H NR (400 MHz, DMSO-d6) δ 1.34-1.42 (m, 6H), 4.21 (q, J=7.2 Hz, 2H), 4.40 (q, J=7.2 Hz, 2H), 7.52 (d, J=2.8 Hz, 1H), 7.56-7.59 (m, 1H), 8.02 (d, J=8.8 Hz, 1H), 8.94 (s, 1H). MS 280, 282 (MH+).

Sources & evidence

ORD record: ord-734edbc24b0b414dab3a7c06a41a001a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09049878B2

Reaction notes

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