Thionyl Chloride → HCID 178498566, compound

HRID 323635Notes

Reaction equation

[C:1]([C:5]1[C:6]([C:17]([OH:19])=O)=[N:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([Cl:16])[CH:9]=2)([O:3][CH3:4])=[O:2].S(Cl)([Cl:22])=O>>[C:1]([C:5]1[C:6]([C:17]([Cl:22])=[O:19])=[N:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([Cl:16])[CH:9]=2)([O:3][CH3:4])=[O:2]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 178498606HCID 178498606, compound

Product 1

HCID 178498566HCID 178498566, compound

Procedure

Concurrently, 3-carbomethoxy-7-chloro-4-hydroxyquinoline-2-carbonyl chloride was prepared from 3-carbomethoxy-7-chloro-4-hydroxyquinoline-2-carboxylic acid (121 mg, 0.43 mM) by heating to 60° C. in thionyl chloride (4 mL). After 3 hours the crude acid chloride was isolated by distilling away the excess thionyl chloride. The crude 3-carbomethoxy-7-chloro-4-hydroxyquinoline-2-carbonyl chloride (130 mg, 0.43 mM) was then placed in anhydrous tetrahydrofuran (3 mL) at ambient temperature and added via cannula to the 4-(trifluoromethoxy)phenylhydrazine solution. After 30 minutes the reaction mixture was poured into 1.0N hydrochloric acid producing a precipitate. The solid was isolated to yield the title compound (185 mg, 95%) as an off-white solid, mp 346-350° C.; MS 456 (M+H). 1H NMR 12.67 (s, 1H, exchangeable), 10.79 (s, 1H, exchangeable), 8.37 (br s, 1H, exchangeable), 8.13 (d, J=8.61 Hz, 1H), 7.83 (d, J=1.76 Hz, 1H), 7.48 (dd, J=8.61, 1.76 Hz, 1H), 7.21 (d, J=8.50 Hz, 2H), 6.94 (d, J=8.50 Hz, 2H), 3.70 (s, 3H).

Workup

customAfter 3 hours the crude acid chloride was isolated

Sources & evidence

ORD record: ord-c49c89677f1e43119b2ae39139975e7e
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06214826B1

Reaction notes

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