1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Ethyl 7-hydroxyquinoline-3-carboxylate

HRID 1748370ノート

反応式

HRID 1748370 の反応式
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12]C)=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.COC1C=C(NC=C(C(OCC)=O)C(OCC)=O)C=CC=1>>[OH:12][C:8]1[CH:7]=[C:6]2[C:11]([CH:2]=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:4]=[N:5]2)=[CH:10][CH:9]=1

参加物

4

反応物 3

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 3904966Diethyl 2-(((3-methoxyphenyl)amino)methylene)malonateHCID 178469633HCID 178469633、化合物

生成物 1

HCID 135819170Ethyl 7-hydroxyquinoline-3-carboxylate収率 90%

実験手順

Ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate. To a solution of boiling Dowtherm™ (100 mL) was added diethyl 2-(((3-methoxyphenyl)amino)methylene)malonate (20.0 g, 68.3 mmol). After 15 minutes the reaction was cooled to ambient temperature and poured into hexanes (500 mL). The precipitate was collected by filtration and dried under high vacuum to yield the title compound as a brown solid (15.2 g, 90%). 1H NMR (400 MHz, DMSO-d6) δ 12.09 (d, J=5.9 Hz, 1H), 8.47 (d, J=6.7 Hz, 1H), 8.03 (d, J=9.4 Hz, 1H), 7.04-6.97 (m, 2H), 4.18 (q, J=7.0 Hz, 2H), 3.85 (s, 3H), 1.25 (t, J=7.2 Hz, 4H).

後処理

  1. filtrationThe precipitate was collected by filtration
  2. customdried under high vacuum

出典と根拠

ORDレコード
ord-459b2d28601b455a9965065114d42db6
出典データセット
uspto-grants-2015_10
特許番号
US09150572B2

反応ノート

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