Phosphorus oxychloride → 2-Chloroquinoline-4-carboxylic acid

Reaction equation

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

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178524625HCID 178524625, compound

Product 1

HCID 2305822-Chloroquinoline-4-carboxylic acid

Procedure

2-Hydroxyquinoline-4-carboxylic acid (34, 2.57 g, 13.6 mmol) and POCl3 (25 mL) were refluxed for 24 h. The reaction mixture was poured onto crushed-ice (300 g). The solid that separated was filtered, washed with water, and dried well under high vacuum afforded 2.47 g (87%) white flasks of desired product. 1H NMR (CDCl3, 300 MHz): δ 8.67 (d, 1H, J=8.4 Hz), 7.91 (d, 1H, J=8.1 Hz), 7.83 (s, 1H), 7.76 (t, 1H, J=7.2 Hz), 7.54 (t, 1H, J=7.2 Hz); LCMS (m/z): 208 (MH+).

Workup

additionThe reaction mixture was poured
customThe solid that separated
filtrationwas filtered
washwashed with water
customdried well under high vacuum

Sources & evidence

ORD record: ord-6ed9a6b5b79d4d5a984862aac93150ec
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358259B2

Reaction notes

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