Phosphorus oxychloride → Ethyl 4-chloro-6-propoxyquinoline-3-carboxylate

HRID 2047734Notes

Reaction equation

O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH3:15])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH3:15])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178458202Ethyl 4-hydroxy-6-propoxyquinoline-3-carboxylate

Product 1

HCID 62328167Ethyl 4-chloro-6-propoxyquinoline-3-carboxylate

Procedure

Prepared as in Example 1b from ethyl 4-hydroxy-6-propoxyquinoline-3-carboxylate (Example 14c) and POCl3 as a pale yellow solid. MS 294, 296 (MH+).

Sources & evidence

ORD record: ord-45412097eada4aadb3eee89cf6094bf2
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592592B2

Reaction notes

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