1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 135819170, compound

HRID 1748370Notes

Reaction equation

HRID 1748370 reaction equation
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

Participants

4

Reactant 3

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

Product 1

HCID 135819170HCID 135819170, compoundYield 90%

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-459b2d28601b455a9965065114d42db6
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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