Hydroxyamine hydrochloride → N-hydroxy-3-(3,4-dimethoxyphenyl)-3-phthalimidopropionamide

HRID 9839Notes

Reaction equation

HRID 9839 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])[CH2:12][C:13](O)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[NH2:28][OH:29]>O1CCCC1>[OH:29][NH:28][C:13](=[O:14])[CH2:12][CH:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 103608253-(3,4-Dimethoxyphenyl)-3-phthalimidopropanoic acid

Product 1

HCID 9885689N-hydroxy-3-(3,4-dimethoxyphenyl)-3-phthalimidopropionamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Hydroxy-3-(3,4-dimethoxyphenyl)-3-phthalimidopropionamide was prepared by the procedure of Example 1 from 3-(3,4-dimethoxyphenyl)-3-phthalimidopropanoic acid (1.82 g, 5.12 mmol), N,N′-carbonyldiimidazole (870 mg, 5.39 mmol) and hydroxylamine hydrochloride (391 mg, 5.63 mmol) in tetrahydrofuran (8 mL) to afford N-hydroxy-3-(3,4-dimethoxyphenyl)-3-phthalimidopropionamide as a white solid (1.52 g, 80% yield): mp, 186.5–188.0° C.; 1H NMR (DMSO-d6) δ 3.12 (d, J=7.8 Hz, 2H, CH2), 3.72 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 5.69 (t, J=7.8 Hz, 1H, NCH), 6.91–6.92 (m, 2H, Ar), 7.03 (br s, 1H, Ar), 7.85 (br s, 4H, Ar), 8.82 (s, 1H, OH), 10.62 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 34.33, 50.25, 55.52, 111.27, 111.67, 119.65, 123.17, 131.26, 134.63, 148.41, 148.56, 166.07, 167.69. Anal. Calcd for C19H18N2O6: C, 61.62; H, 4.90; N, 7.56. Found: C, 61.29; H, 4.72; N, 7.47.

Sources & evidence

ORD record
ord-66da087430004165808bba7fc1ca6188
Source dataset
uspto-grants-2006_08
Patent number
US07091356B2

Reaction notes

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