Water → 1H-Indole-3-ethanamine, 5-nitro-

HRID 1666841Notes

Reaction equation

HRID 1666841 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].O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10]([NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][NH2:15])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 2477542-(5-nitro-1H-indol-3-yl)acetonitrile

Product 1

HCID 1512951H-Indole-3-ethanamine, 5-nitro-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve (5-nitro-1H-indol-3-yl)-acetonitrile (9 g, 44.7 mmol) in 250 mL dry THF and treat with 90 mL 1 M BH3 in THF at ambient temperature. Stir overnight and quench the reaction cautiously by the dropwise addition of 10 mL water. Concentrate to dryness under vacuum and partition the residuc between 5 N HCl and EtOAc. Extract the aqueous layer with EtOAc and combine with the original EtOAc layer. Treat the aqueous layer with 5 N NaOH and extract 3 times with 10% MeOH in EtOAc. Purify by flushing the extracts through a pad of 100 g SCX ion exchange resin, rinsing with 2 liters of MeOH which was discarded, and then eluting with the 2 M NH3 in MeOH and concentrating to give the title compound as a dark solid: ISMS 206 (M+1); Analysis for C20H18F6N2O2 0.3H2O 0.1C7H8: calcd: C, 57.34; H, 5.74; N, 19.29. found: C, 57.30; H, 5.38; N, 19.08. 1H NMR (DMSO-d6) 11.9-11.2 (bs, 1H), 8.50-8.49 (d, 1H), 7.95-7.92 (m, 1H), 7.47-7.45 (m, 1H), 7.38 (s, 1H), 2.79 (s, 4H), 2.2-1.3 (bs, 2H).

Workup

  1. additiontreat with 90 mL 1 M
  2. customat ambient temperature
  3. customquench
  4. customthe reaction
  5. concentrationConcentrate to dryness under vacuum
  6. custompartition the residuc between 5 N HCl and EtOAc
  7. extractionExtract the aqueous layer with EtOAc
  8. additionTreat the aqueous layer with 5 N NaOH
  9. extractionextract 3 times with 10% MeOH in EtOAc
  10. customPurify
  11. customby flushing the extracts through a pad of 100 g SCX ion exchange resin
  12. washrinsing with 2 liters of MeOH which
  13. washeluting with the 2 M NH3 in MeOH
  14. concentrationconcentrating

Sources & evidence

ORD record
ord-377bb9e3beaa48bbb9ebe0b1af9de17a
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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