Hydroxyamine hydrochloride → N-hydroxy-8-(4-methoxyphenyl)-8-oxooctanamide

HRID 1182467Notes

Reaction equation

HRID 1182467 reaction equation
[C:1]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH2:20][OH:21].Cl>C(N(CC)CC)C>[OH:21][NH:20][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:1](=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 109014778-(4-Methoxyphenyl)-8-oxooctanoic acid

Product 1

HCID 10923922N-hydroxy-8-(4-methoxyphenyl)-8-oxooctanamideYield 48%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure described in Example 14, step 3, but substituting carboxylic acid 50b for 37 and using 1.1 equivalent of NH2OH.HCl and triethylamine each, the title compound was obtained as light yellow solid in 48% yield: 1H NMR (300 MHz, CD3OD/CDCl3=5/1) δ 7.94 (d, J=9.0 Hz, 2H), 6.95 (d, J=9.0 Hz, 2H), 3.88 (s, 3H), 2.93 (t, J=7.2 Hz, 2H), 2.11 (t, J=7.5 Hz, 2H), 1.59-1.79(m, 4H), 1.37 (m, 4H); 13C NMR (75.4 MHz, CD3OD/CDCl3=5/1) δ 24.15, 25.04, 28.59(2), 32.51, 37.88, 55.21, 113.54, 129.58, 130.20, 163.39, 171.10, 200.06.

Sources & evidence

ORD record
ord-2bbfc9d025924d8ca99d3e2954a8bfe5
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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