Hydrochloric Acid → N-hydroxy-4-[2-(phenylformamido)ethoxy]benzamide

HRID 29698Notes

Reaction equation

HRID 29698 reaction equation
[C:1]1([C:7]([NH:9][CH2:10][CH2:11][O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17](OC)=[O:18])=[CH:15][CH:14]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][OH:24].[OH-].[Na+].Cl>C1COCC1.CO>[OH:24][NH:23][C:17](=[O:18])[C:16]1[CH:21]=[CH:22][C:13]([O:12][CH2:11][CH2:10][NH:9][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:8])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 14426627Methyl 4-(2-benzenecarbonylamino-ethoxy)benzoate

Product 1

HCID 24971308N-hydroxy-4-[2-(phenylformamido)ethoxy]benzamide

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of crude methyl 4-(2-benzenecarbonylamino-ethoxy)benzoate (0.5 mmol) in a 1:1 mixture of THF/methanol (20 ml) was added 50 wt. % aqueous hydroxylamine (3 ml) followed by 1M aqueous NaOH (1 ml) adjusting the pH between 10-11. The reaction mixture was stirred for 14 h, neutralized to pH=7-8 with 6 M aqueous HCl and concentrated in vacuo. The precipitate was collected and purified by HPLC providing the title compound as a white solid. 1H NMR (DMSO-d6): δ 8.69 (t, J=5.8 Hz, 1H), 7.83 (d, J=7.5 Hz, 2H), 7.69 (d, J=9.1 Hz, 2H), 7.46 (m, 3H), 6.99 (d, J=9.1 Hz, 2H), 4.16 (t, J=5.8 Hz, 2H), 3.63 (q, J=5.8 Hz, 2H). EM (calc.): 300.1; MS (ESI) m/e: 301.1 (M−1)+, 299.0 (M+1)−.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe precipitate was collected
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-549d849cf1bb46a8a775f5fe08a68aae
Source dataset
uspto-grants-2008_09
Patent number
US07420089B2

Reaction notes

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