Bromine → Methyl 3,8-dibromo-5-methoxyquinoline-6-carboxylate

HRID 451245

Reaktionsgleichung

Reaktionsgleichung von HRID 451245
[Br:1][C:2](=[CH2:5])[CH:3]=O.BrBr.[NH2:8][C:9]1[C:18]([Br:19])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:20][CH3:21])[CH:10]=1>CC(O)=O>[Br:1][C:2]1[CH:3]=[N:8][C:9]2[C:10]([CH:5]=1)=[C:11]([O:20][CH3:21])[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][C:18]=2[Br:19]

Komponenten

5

Edukt 3

HCID 24408BromineHCID 269692-Propenal, 2-bromo-HCID 2768028Methyl 4-amino-5-bromo-2-methoxybenzoate

Produkt 1

HCID 67127342Methyl 3,8-dibromo-5-methoxyquinoline-6-carboxylateAusbeute 33,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

step 1—Bromine (4.48 mL, 86.9 mmol) in HOAc (50 mL) was added to a solution of 2-bromoacrylaldehyde (11.7 g, 86.9 mmol, CASRN 111049-68-4) in HOAc (100 mL) at RT until the solution showed faint Br2 color. To this solution was added methyl 4-amino-5-bromo-2-methoxybenzoate (22.6 g, 86.9 mmol) and the resulting solution was gradually heated to 100° C. After the temperature reached 100° C., stirring was continued for 15 min then the solution was cooled and concentrated in vacuo. The reaction mixture was neutralized with satd. aq. NaHCO3 and the resulting solid was filtered and washed with water. The solid was washed with ether followed by 10% MeOH/DCM to afford 11.04 g of 122a. The filtrate was absorbed onto SiO2 and purified on a flash column eluting with a DCM/hexane gradient (50 to 100% DCM to afford an additional 3.46 g of 122a.

Aufarbeitung

  1. customreached 100° C.
  2. temperaturethe solution was cooled
  3. concentrationconcentrated in vacuo
  4. filtrationaq. NaHCO3 and the resulting solid was filtered
  5. washwashed with water
  6. washThe solid was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-45e34d1bc3c34c8e8895b2cc6b8467b6
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487103B2

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