Phenethylamine → N,2-dimethylquinolin-4-amine

HRID 2223712노트

반응식

HRID 2223712 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.C([CH2:20][NH2:21])C1C=CC=CC=1>C(Cl)Cl>[CH3:20][NH:21][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1

참가 물질

4

반응물 2

HCID 1001PhenethylamineHCID 779734-Chloro-2-methylquinoline

생성물 1

HCID 13042979N,2-dimethylquinolin-4-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
120 °C

실험 절차

A mixture of 4-chloro-2-methyl-quinoline (4.36 g, 24.5 mmol) and benzylmethylamine (3.13 g, 25.8 mmol) is heated under N2 at 120° C. for 12 h. The residue is dissolved in CH2Cl2 (50 ml) and washed successively with aqueous saturated Na2CO3 (50 mL) and 1M aqueous NaOH (50 ml). The CH2Cl2 layer is evaporated, and the residue is dissolved in MeOH (400 mL) and 4M HCl in dioxane (12 mL). 10% Pd—C (410 mg) are added and the suspension is hydrogenated for 15 h under ambient pressure. The reaction mixture is filtered through a pad of Celite. 1M aqueous NaOH (100 mL) is added and the filtrate is evaporated. The residue is dissolved in water and extracted with CH2Cl2 (3×50 mL). The combined organic extracts are dried and evaporated to provide the title compound.

후처리

  1. washwashed successively with aqueous saturated Na2CO3 (50 mL) and 1M aqueous NaOH (50 ml)
  2. customThe CH2Cl2 layer is evaporated
  3. dissolutionthe residue is dissolved in MeOH (400 mL)
  4. addition10% Pd—C (410 mg) are added
  5. filtrationThe reaction mixture is filtered through a pad of Celite
  6. addition1M aqueous NaOH (100 mL) is added
  7. customthe filtrate is evaporated
  8. dissolutionThe residue is dissolved in water
  9. extractionextracted with CH2Cl2 (3×50 mL)
  10. customThe combined organic extracts are dried
  11. customevaporated

출처 및 근거

ORD 기록
ord-07fae472ac6a45529910ad6bd2bbe3a3
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375227B2

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