Sodium Hydroxide → HCID 86040275, compound

HRID 1392263Notes

Reaction equation

HRID 1392263 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=O)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl.[CH2:23]([O:26][NH2:27])[CH:24]=[CH2:25]>C(O)C>[CH2:23]([O:26][N:27]=[CH:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2621041-benzyl-1H-indole-3-carbaldehydeHCID 16211718O-Prop-2-en-1-ylhydroxylamine--hydrogen chloride--water (1/1/1)

Product 1

HCID 86040275HCID 86040275, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-benzyl-1H-indole-3-carbaldehyde (1.086 g, 4.61 mmol) in 4:1 ethanol:2.5 M NaOH solution (16 mL) was added O-allyl hydroxylamine hydrochloride hydrate(0.768 g, 7.17 mmol). The reaction mixture was heated to reflux for 30 minutes and allowed to cool back down to room temperature. The reaction mixture was concentrated to a small volume and the pH of the mixture was then adjusted to 7 using 2 M hydrochloric acid. The mixture was extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude oil was purified by flash chromatography through silica gel using ethyl acetate/hexanes (10/90) to give 1-benzyl-1H-indole-3-carbaldehyde O-allyl-oxime (0.176 g, 88%) as a colorless oil. 1H NMR (400 MHz, CDCl3); δ 8.30(s, 1H), 8.15 (m, 1H), 7.24 (m, 7H), 7.10 (d, 2H), 6.10 (m, 1H), 5.30 (m, 4H), 4.68 (d, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 minutes
  3. concentrationThe reaction mixture was concentrated to a small volume
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude oil was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-bf2aaf3190244b318a9712d626af1b67
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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