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

HRID 2165537Notes

Reaction equation

HRID 2165537 reaction equation
[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]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 151761385-Nitro-1H-indole-3-carboxamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

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 ).

Workup

  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

Sources & evidence

ORD record
ord-b4ba1f7cd7a342f39e378925e6797a4c
Source dataset
uspto-grants-1990_07
Patent number
US04940703

Reaction notes

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