Ethanol → HCID 178504228, compound

HRID 1501420Notes

Reaction equation

HRID 1501420 reaction equation
[CH3:1][Si:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][CH:14]=[C:15]([C:16]#[N:17])[C:10]=2[CH:9]=[CH:8]1.C(O)C.Cl.[NH2:24][OH:25].C(=O)([O-])[O-].[K+].[K+]>>[OH:25][NH:24][C:16]([C:15]1[C:10]2[CH:9]=[CH:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:19])([CH3:18])[CH3:1])[C:11]=2[N:12]=[CH:13][CH:14]=1)=[NH:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 574776601-[2-(Trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Product 1

HCID 178504228HCID 178504228, compoundYield 97.9%

Procedure

1-[2-(Trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (0.05 g, 0.0002 mol) was dissolved in ethanol (2.0 mL, 0.034 mol), and then hydroxylamine hydrochloride (0.023 g, 0.00033 mol) and potassium carbonate (0.10 g, 0.00073 mol) were added. The reaction was heated to reflux for 5 h, and the reaction was then allowed to cool to rt and filtered to remove the solids. The filtrate was concentrated to give the product 0.06 g as yellow oily residue, LC/MS (M+H)+ 307.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 h
  3. filtrationfiltered
  4. customto remove the solids
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d3b68a5c1a5140bdabf1b688ba2432d6
Source dataset
uspto-grants-2015_12
Patent number
US09206187B2

Reaction notes

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