Benzoyl chloride → N-hydroxy-7-(4-methoxyphenyl)-7-oxoheptanamide

HRID 1182489Notes

Reaction equation

HRID 1182489 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]I)C.C(OC(=O)CCCCCCI)C.[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1.C(Cl)(=O)C1C=CC=CC=1.[NH2:44][OH:45].Cl>C(N(CC)CC)C>[OH:45][NH:44][C:4](=[O:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([O:25][CH3:24])=[CH:27][CH:28]=1

Participants

7

Reactant 5

HCID 7412Benzoyl chlorideHCID 7477p-Anisoyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 10660673Ethyl 7-iodoheptanoateHCID 10880140Ethyl 6-iodohexanoate

Product 1

HCID 10858374N-hydroxy-7-(4-methoxyphenyl)-7-oxoheptanamideYield 54%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure described in Example 18, step 1, 2, 3, but substituting respectively ethyl-6-iodohexanoate for ethyl-7-iodoheptanoate and 4-methoxybenzoyl chloride for benzoyl chloride, and then the resulting carboxylic acid was substituted for 37 in Example 14, step 3, using 1.1 equivalent of NH2OH.HCl and triethylamine each, to afford the title compound 110 in 54% yield. 1H NMR (300 MHz, 20% CD3OD in CDCl3): δ 7.86 (d, J=8.7 Hz, 2H), 6.88 (d, J=8.7 Hz, 2H), 3.81 (s, 3H), 2.87 (t, J=6.6 Hz, 2H), 2.07 (br t, 2H), 1.62 (m, 4H), 1.34 (m, 2H). 13C NMR (75 MHz, 20% CD3OD in CDCl3): δ 23.68, 24.96, 28.32, 32.28, 37.63, 55.14, 113.49, 129.48, 130.13, 163.35, 171.06, 199.81.

Sources & evidence

ORD record
ord-11ba5d3f4ebf4189954e899360c24fb0
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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