Tetrahydrofuran → HCID 178498566、化合物

反応式

O1CCCC1.[C:6]([C:10]1[C:11]([C:22]([OH:24])=O)=[N:12][C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][CH:16]=[C:15]([Cl:21])[CH:14]=2)([O:8][CH3:9])=[O:7].S(Cl)([Cl:27])=O>>[C:6]([C:10]1[C:11]([C:22]([Cl:27])=[O:24])=[N:12][C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][CH:16]=[C:15]([Cl:21])[CH:14]=2)([O:8][CH3:9])=[O:7]

参加物

反応物 3

HCID 8028Tetrahydrofuran

HCID 24386Thionyl Chloride

HCID 178498606HCID 178498606、化合物

生成物 1

HCID 178498566HCID 178498566、化合物

反応条件

温度: 0 °C

実験手順

The free base of 4-(trifluoromethoxy)phenyl hydrazine was prepared from thehydrochloride salt by treatment of the suspended salt (400 mg, 1.75 mM) in ethyl acetate (50 mL) with 2N sodium hydroxide(50 mL). The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo to provide the free base of 4-(trifluoromethoxy)phenyl hydrazine (325 mg, 1.69 mK). This material was placed into anhydrous tetrahydrofuran (5 mL) and cooled to 0° C. under a nitrogen atmosphere. 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 crude3-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)phenyl hydrazine 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).

後処理

customAfter 3 hours the crude acid chloride was isolated

出典と根拠

ORDレコード: ord-fc3ac25425eb41b389af815dc8023947
出典データセット: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05744471

反応ノート

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