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

HRID 912620ノート

反応式

HRID 912620 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 67127342Methyl 3,8-dibromo-5-methoxyquinoline-6-carboxylate収率 33.9%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bc37b7f6f5ad4715ad4d00189a31e94e
出典データセット
uspto-grants-2011_09
特許番号
US08026253B2

反応ノート

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