Bromine → 4-Chloroquinolin-2-amine

HRID 1791948ノート

反応式

HRID 1791948 の反応式
BrBr.[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6](C(N)=O)[CH:5]=1.Cl.Cl.Cl.COC(C1C=C(N2CCN([C@@H]3CN[C@H](C(N4CCSC4)=O)C3)CC2)C2C(=CC=CC=2)[N:25]=1)=O>[OH-].[K+].O1CCCC1>[NH2:25][C:6]1[CH:5]=[C:4]([Cl:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

参加物

6

反応物 3

HCID 24408BromineHCID 220292874-Chloro-2-quinolinecarboxamideHCID 67508184HCID 67508184、化合物

生成物 1

HCID 140674074-Chloroquinolin-2-amine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 14797Potassium Hydroxide溶媒

実験手順

Bromine (2.32 mL) was dissolved in 5% aqueous potassium hydroxide solution (190 mL), and a solution of 4-chloroquinoline-2-carboxamide [product of Example 262 (1), 9.80 g] in tetrahydrofuran (190 mL) was dropwise added thereto. The mixture was stirred at room temperature for 30 min, and the mixture was stirred at 80° C. for 1 hr with heating. The reaction mixture was filtrated and the filtrate was added to water. The mixture was extracted with chloroform, and the extract was washed with brine and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 2-amino-4-chloroquinoline (1.98 g) as a pale-yellow solid.

後処理

  1. stirringthe mixture was stirred at 80° C. for 1 hr
  2. temperaturewith heating
  3. filtrationThe reaction mixture was filtrated
  4. additionthe filtrate was added to water
  5. extractionThe mixture was extracted with chloroform
  6. washthe extract was washed with brine
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-ce7bfe590e3a4a64a00c07b68f3053f5
出典データセット
uspto-grants-2006_07
特許番号
US07074794B2

反応ノート

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