Water → 5-Amino-1-chloroisoquinoline

HRID 1181407

반응식

HRID 1181407 반응식
[BH4-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([N+:14]([O-])=O)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1.O>C(O)C.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Cu]>[Cl:3][C:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([NH2:14])[C:8]=2[CH:7]=[CH:6][N:5]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 4597741-Chloro-5-nitroisoquinolineHCID 4311764Sodium borohydride2회

생성물 1

HCID 4597715-Amino-1-chloroisoquinoline수율 24.3%

시약·촉매·용매 2

HCID 5363992Copper, bis(2,4-pentanedionato-O,O')-, (SP-4-1)-촉매HCID 702Ethanol용매2회

실험 절차

Copper (II) acetylacetonate (253 mg) was suspended in ethanol (10 ml) and sodium borohydride (366 mg) was added in one portion. The mixture was stirred for 5 minutes, by which time a black suspension had appeared. A suspension of 1-chloro-5-nitroisoquinoline (Description 47; 1.01 g, 4.84 mmol) in ethanol (20 ml) was then added over 15 minutes whilst cooling in a water bath; the mixture effervesced. The mixture was stirred at room temperature for 1 hour, then more sodium borohydride (160 mg) was added and stirring continued for a further 1 hour. Water (100 ml) was added then the ethanol was evaporated and the mixture extracted with ethyl acetate (3×50 ml). The combined organic layers were dried (Na2SO4) and evaporated. Purification of the residue by flash column chromatography using 5% methanol-dichloromethane as eluant gave the title compound (210 mg).

후처리

  1. additionwas then added over 15 minutes
  2. temperaturewhilst cooling in a water bath
  3. stirringThe mixture was stirred at room temperature for 1 hour
  4. stirringstirring
  5. waitcontinued for a further 1 hour
  6. customthe ethanol was evaporated
  7. extractionthe mixture extracted with ethyl acetate (3×50 ml)
  8. dry with materialThe combined organic layers were dried (Na2SO4)
  9. customevaporated
  10. customPurification of the residue by flash column chromatography

출처 및 근거

ORD 기록
ord-69f909717e754fdab35f2170ee962b7d
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285563B2

연결된 노트

불러오는 중…