Water → HCID 14391136, compound

HRID 1381554Notes

Reaction equation

HRID 1381554 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[CH2:13][C:14]#[N:15])([O-:3])=[O:2].[OH-].[Na+].[CH3:18]I.O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH3:18][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([CH2:13][C:14]#[N:15])=[CH:8]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 2477542-(5-nitro-1H-indol-3-yl)acetonitrile

Product 1

HCID 14391136HCID 14391136, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 11.5 g (0.057 mole) of 5-nitroindole-3-acetonitrile and 1.46 g (0.006 mole) of benzyltriethyl ammonium chloride in 120 ml of 50% (aq.) NaOH, stirred at 0°, was added, dropwise over 1.5 hours, a solution of 8.26 g (0.058 mole) of CH3I in 80 ml of CH2Cl2. The temperature was raised to 25° and the stirring continued for 2 hours. The suspension was then poured into 800 ml of H2O and filtered. The CH2Cl2 layer of the filtrate was taken to dryness in vacuo and the resulting yellow solid combined with the solid from the filtration. The combined solids were washed with H2O, dried and recrystallized from n-BuOH to give 9.35 g (76%) of a yellow solid: m.p. 165°-166°; nmr (d6 -DMSO) δ(TMS) 8.54 (1, d, J=2.5 Hz), 8.16 (1, d of d, Jortho =9 Hz, Jmeta =2.5 Hz), 7.37 (1, d, J=9 Hz), 7.29 (1, S), and 3.86 ppm (5, S, N--CH3 and --CH2 --CN).

Workup

  1. additionwas added, dropwise over 1.5 hours
  2. temperatureThe temperature was raised to 25°
  3. filtrationfiltered
  4. filtrationthe resulting yellow solid combined with the solid from the filtration
  5. washThe combined solids were washed with H2O
  6. customdried
  7. customrecrystallized from n-BuOH

Sources & evidence

ORD record
ord-b5e7b9b6ca3340e5b72e363d506410b5
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

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