Benzoyl chloride → N-hydroxy-7-(naphthalen-2-yl)-7-oxoheptanamide

HRID 1182490Notes

Reaction equation

HRID 1182490 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.[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[C:34](Cl)=[O:35].C(Cl)(=O)C1C=CC=CC=1.[NH2:46][OH:47].Cl>C(N(CC)CC)C>[OH:47][NH:46][C:4](=[O:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:34]([C:25]1[CH:26]=[CH:27][C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=1)=[O:35]

Participants

7

Reactant 5

HCID 7412Benzoyl chlorideHCID 752462-Naphthoyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 10660673Ethyl 7-iodoheptanoateHCID 10880140Ethyl 6-iodohexanoate

Product 1

HCID 11129854N-hydroxy-7-(naphthalen-2-yl)-7-oxoheptanamideYield 55%

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 2-naphthoyl 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 111 in 55% yield. 1H NMR (300 MHz, 20% CD3OD in CDCl3): δ 8.47 (s, 1H), 8.05-7.50 (m, 6H), 3.12 (br t, 2H), 2.15 (br t, 2H), 1.82-1.60 (m, 4H), 1.46 (m, 2H). 13C NMR (75 MHz, 20% CD30D in CDCl3): δ 23.59, 25.02, 28.36, 32.33, 38.06, 123.40, 126.56, 127.46, 128.21, 128.29, 129.29, 129.60, 132.25, 133.78, 135.37, 171.04, 201.04.

Sources & evidence

ORD record
ord-a8fa1e7c08dd4c7980148b413788da13
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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