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Triethylamine → 5-nitro-1H-indole-3-carbonitrile

HRID 2165537
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HRID 2165537 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]([NH2:15])=O)([O-:3])=[O:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]#[N:15])([O-:3])=[O:2]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 151761385-Nitroindole-3-carboxamide

생성물 1

HCID 2475435-nitro-1H-indole-3-carbonitrile수율 46%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

5-Nitro-1H-indole-3-carboxamide (2.0 g) was suspended in dry dioxane (100 ml) containing triethylamine (7.8 g). Trifluoroacetic anhydride (8.2 g) was added dropwise with the temperature of the solution maintained at less than 5° C., the reaction was then allowed to warm to room temperature overnight. The reaction mixture was diluted with dichloromethane (200 ml), washed with water (3×100 ml), dried (MgSO4) and the solvent removed. Recrystallisation of the residue from ethyl acetate/hexane afforded the title compound (840 mg), m.p. 186°-190° C. δH (360 MHz, CDCl3) 7.58 (1H, d, J=7.2 Hz, H-7), 7.94 (1H, d, J=1.0 Hz, H-4), 8.16 (1H, dd, J=7.2, 1.0 Hz, H-6), 8.63 (1H, s, H-2); m/z 187 (M+, 100), 157 (45), 141 (95 ), 129 (30), 114 (55), 102 (10), 87 (20 ).

후처리

  1. temperaturemaintained at less than 5° C.
  2. washwashed with water (3×100 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed
  5. customRecrystallisation of the residue from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-b4ba1f7cd7a342f39e378925e6797a4c
출처 데이터셋
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04940703

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