Benzoyl chloride → N-Hydroxy-6-[(2-indolyl)carbonyl]hexanamide

HRID 1182491Notes

Reaction equation

HRID 1182491 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.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[C:33](Cl)=[O:34].C(Cl)(=O)C1C=CC=CC=1.[NH2:45][OH:46].Cl>C(N(CC)CC)C>[OH:46][NH:45][C:4](=[O:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:33]([C:25]1[NH:24][C:32]2[C:27]([CH:26]=1)=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:34]

Participants

7

Reactant 5

HCID 7412Benzoyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 10660673Ethyl 7-iodoheptanoateHCID 10880140Ethyl 6-iodohexanoateHCID 118162081H-indole-2-carbonyl Chloride

Product 1

HCID 58982196N-Hydroxy-6-[(2-indolyl)carbonyl]hexanamideYield 35%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure described in Example 1, step 4, but substituting indole-2-carboxylic acid for 5, followed by Example 18, step 1, 2, 3, but substituting respectively ethyl-6-iodohexanoate for ethyl-7-iodoheptanoate and indole-2-carbonyl 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 112 in 35% yield. 1H NMR: (300 MHz, CDCl3) δ 7.62 (m, 2H), 7.20-7.00 (m, 3H), 2.82 (m, 2H), 2.00 (m, 2H), 1.62 (m, 2H), 1.22 (m, 4H).

Sources & evidence

ORD record
ord-d3c2f720861448d89d3049242a21cf91
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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