Potassium Hydroxide → HCID 178515628, compound

HRID 1057155Notes

Reaction equation

HRID 1057155 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([O:12]CC)=O)=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17].[OH-].[K+]>CO>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:17][N:16]=[C:10]([OH:12])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 66800188Ethyl 3-(4-iodophenyl)propiolate

Product 1

HCID 178515628HCID 178515628, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(4-iodophenyl)propiolate (420 mg, 1.39 mmol) in MeOH (10 mL), were added hydroxylamine hydrochloride (391 mg, 5.20 mmol) and KOH (5 M in methanol, 1.7 mL, 8.5 mmol). The mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was redissolved in water (15 mL) and acidified with 2 M aqueous HCl to pH 2˜3. The precipitate was collected by filtration to afford the title compound (228 mg, 57%). 1H NMR (DMSO-d6, 400 MHz): δ 11.51 (brs, 1H), 7.94 (d, 2H), 7.65 (d, 2H), 6.67 (s, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was redissolved in water (15 mL)
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-086402469f56452c80b015500ec38e03
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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