Bromine → 4-Chloroquinolin-2-amine

HRID 1791948노트

반응식

HRID 1791948 반응식
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

참가 물질

6

반응물 3

HCID 24408BromineHCID 220292874-Chloro-2-quinolinecarboxamideHCID 67508184HCID 67508184, 화합물

생성물 1

HCID 140674074-Chloroquinolin-2-amine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 14797Potassium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ce7bfe590e3a4a64a00c07b68f3053f5
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074794B2

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