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

HRID 1748370노트

반응식

HRID 1748370 반응식
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

참가 물질

4

반응물 3

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

생성물 1

HCID 135819170Ethyl 7-hydroxyquinoline-3-carboxylate수율 90%

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-459b2d28601b455a9965065114d42db6
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150572B2

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