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Sodium Chloride → 6-chloro-4-fluoro-9H-beta-carbolin-8-ylamine

HRID 12237
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HRID 12237 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:15]([O-])=O)[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([F:18])[C:5]2=1.C([O-])=O.[NH4+].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(O)C.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:15])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([F:18])[C:5]2=1
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참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 2723923Ammonium formateHCID 671659696-chloro-4-fluoro-8-nitro-9H-beta-carboline

생성물 1

HCID 593375386-chloro-4-fluoro-9H-beta-carbolin-8-ylamine수율 70.3%

시약·촉매·용매 2

HCID 702
Ethanol
용매
HCID 887Methanol용매

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온도
75 °C

실험 절차

Sulfated platinum (˜0.1 eq, 1 g) was added to a suspension of 6-chloro-4-fluoro-8-nitro-9H-β-carboline (1.0 eq, 35 mmol, 9.3 g) and ammonium formate (3.0 eq, 105 mmol, 6.6 g) in ethanol (175 mL) and the resulting mixture heated at 75° C. for 4 h. After cooling to RT the mixture was filtered through a short plug of Celite® washing with copious amounts of methanol, and then the filtrate concentrated in vacuo to afford a beige solid. The solid was suspended in the minimum volume of methanol and added dropwise to a vigorously stirred mixture of saturated sodium bicarbonate solution and saturated sodium chloride solution. After stirring for 15 min the precipitated solids were collected by suction filtration, washed with water (200 mL) and dried in vacuo to afford 6-chloro-4-fluoro-9H-β-carbolin-8-ylamine (5.8 g, 70% 2 steps) as a beige powder.

후처리

  1. temperatureAfter cooling to RT the mixture
  2. filtrationwas filtered through a short plug of Celite®
  3. washwashing with copious amounts of methanol
  4. concentrationthe filtrate concentrated in vacuo
  5. customto afford a beige solid
  6. filtrationwere collected by suction filtration
  7. washwashed with water (200 mL)
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-534f3688ab12471ab15900e5214ec6b6
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07727985B2

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