Sodium Hydroxide → HCID 66800424, compound

HRID 1057158Notes

Reaction equation

HRID 1057158 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.Cl.[NH2:17]O.[OH-].[Na+]>O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][C:10](=[O:11])[O:12][N:17]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 3593589ethyl 3-(4-iodophenyl)-3-oxopropanoate

Product 1

HCID 66800424HCID 66800424, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 3-(4-iodophenyl)-3-oxopropanoate (3.0 g, 9.4 mmol) was added slowly to a solution of hydroxylamine hydrochloride (660 mg, 9.44 mmol), NaOH (795 mg, 19.8 mmol), and water (12 mL) at 0° C. The reaction mixture was kept at 0° C. for 1 h. The precipitate was collected by filtration, rinsed with water, and dried under vacuum to afford the title compound as white solid (2.0 g, 64%). 1H NMR (CDCl3, 400 MHz): δ 7.84 (d, 2H), 7.40 (d, 2H), 3.78 (s, 2H). 13C NMR (acetone-d6, 100 MHz): δ 176.1, 164.6, 139.1, 129.2, 129.0, 98.6, 34.4.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washrinsed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-45d9cf82bc014f7ca33beefc077d8330
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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