Water → 2-(7-nitro-1H-indol-3-yl)ethan-1-amine

HRID 1371967Notes

Reaction equation

HRID 1371967 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH2:13][C:14]#[N:15])([O-:3])=[O:2].O>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH2:13][CH2:14][NH2:15])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 21071616(7-nitro-1H-indol-3-yl)acetonitrile

Product 1

HCID 210714282-(7-nitro-1H-indol-3-yl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve in a 500 mL round bottom flask equipped with magnetic stirring, and a nitrogen inlet, (7-nitro-1H-indol-3-yl)-acetonitrile (5.27 g, 26 mmol) in dry tetrahydrofuran (150 mL). Treat the solution with 1M BH3:THF (55 mL, 55 mmol) and stir at room temperature. After 20 hours, quench the reaction by the cautious dropwise addition of water (9 mL) and stir until foaming and gas evolution has stopped. Concentrate the mixture to dryness in vacuo, redissolve in 1 N HCl (300 ml) and extracte with ethyl acetate. Basify the aqueous phase 5 N NaOH and extract with ethyl acetate. Pool the ethyl acetate extracts and dry over sodium sulfate and concentrate in vacuo to give the title compound as an orange-brown solid: 1H NMR (400 MHz, dmso-d6): 11.66 (br s, 1H) 8.07 (t, 2H, J=7.6 Hz), 7.32 (s, 1H), 7.20 (t, 1H, J=8.0 Hz) 2.79–2.83 (m, 4H), MS (APCI):m/e 189.0 (M-NH2).

Workup

  1. dissolutionDissolve in a 500 mL round bottom flask
  2. additionTreat the solution with 1M
  3. customquench
  4. customthe reaction
  5. concentrationConcentrate the mixture to dryness in vacuo
  6. dissolutionredissolve in 1 N HCl (300 ml) and extracte with ethyl acetate
  7. extractionextract with ethyl acetate
  8. dry with materialPool the ethyl acetate extracts and dry over sodium sulfate
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-2cd6e15c6e254e18a336746c3e997638
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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