2-Aminobenzonitrile → 4-Aminoquinoline

HRID 392631

반응식

HRID 392631 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C(O)(=O)C.N1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][CH:16]=1.[NH2:24][C:25]1C=CC=C[C:26]=1C#N>C1COCC1>[NH2:24][C:25]1[C:19]2[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:17]=[CH:16][CH:26]=1

참가 물질

5

반응물 3

HCID 729132-AminobenzonitrileHCID 2733832Lithium HexamethyldisilazideHCID 67199695Benzimidazole acetate

생성물 1

HCID 684764-Aminoquinoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

LiHMDS (3-4 eq) was added to the benzimidazole acetate (1.0 eq) in THF (at a constant temperature ranging from −78° C. to 0° C.). After 20 minutes, a solution of the 2-aminobenzonitrile (1.1 eq) in THF was then added. The resulting mixture was allowed to warm to room temperature, stirred for 1-3 hours and was then heated to approx. 40° C.-65° C.(1 hour to 12 hours). The mixture was cooled to 0° C. and quenched with NH4Cl (aq, saturated). The aqueous phase was extracted with Ch2Cl2 or EtOAc, and the organic extracts were collected, dried (Na2SO4), and filtered. Evaporation of the solvent under reduced pressure and purification of the residue by silica gel chromatography or HPLC provided the 4-amino quinoline products.

후처리

  1. customranging from −78° C. to 0° C.
  2. temperaturewas then heated to approx. 40° C.-65° C.(1 hour to 12 hours)
  3. temperatureThe mixture was cooled to 0° C.
  4. customquenched with NH4Cl (aq, saturated)
  5. extractionThe aqueous phase was extracted with Ch2Cl2 or EtOAc
  6. customthe organic extracts were collected
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customEvaporation of the solvent
  10. customunder reduced pressure and purification of the residue by silica gel chromatography or HPLC

출처 및 근거

ORD 기록
ord-cb4a92211ca7435d99b3046171b4a071
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800760B2

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