ethyl (2Z)-3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate → HCID 57617105, compound

HRID 1360104Notes

Reaction equation

HRID 1360104 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]/[C:9](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10]\[C:11]([O:13]CC)=O)=[CH:4][C:3]=1[O:22][CH3:23]>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:22][CH3:23])[NH:8][C:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:10][C:11]2=[O:13]

Participants

3

Reactant 1

HCID 57617098ethyl (2Z)-3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate

Product 1

HCID 57617105HCID 57617105, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent2×

Procedure

To refluxing (˜300° C.) dowtherm A (100 ml) (mixture of biphenyl and diphenyl ether) was added ethyl (2Z)-3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate (6.5 g, 17.27 mmol) in DOWTHERM A (5 mL, washed with 1 mL). Almost immediately, white solid begins to precipitate out of solution. Refluxing was continued for 40 min, and the reaction was cooled to RT and let stand for 1 h. The white solid was then filtered off, and the washed extensively with hexanes to give 6-bromo-7-methoxy-2-phenylquinolin-4(1H)-one as white crystals (4.72 g, 83%). 1H NMR (400 MHz, DMSO-d6): 11.69 (s, 1H), 8.19 (s, 1H), 7.82 (m, 2H), 7.59 (m, 3H), 7.35 (s, 1H), 6.33 (s, 1H), 3.96 (s, 3H). LRMS (CI, [M+H]) Calc'd=330.0. found=330.1.

Workup

  1. customto precipitate out of solution
  2. temperatureRefluxing
  3. waitlet stand for 1 h
  4. filtrationThe white solid was then filtered off
  5. washthe washed extensively with hexanes

Sources & evidence

ORD record
ord-39ad1d16d2864bedbf0768710d8694f9
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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