Triethylamine → 84636-23-7

HRID 521288Notes

Reaction equation

HRID 521288 reaction equation
NCCCCCCCCCCCC(O)=O.S(Cl)([Cl:18])=O.Cl[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][C:22]=1[N+:31]([O-:33])=[O:32].Cl.[NH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48].C(N(CC)CC)C>ClCCl.C(O)C>[ClH:18].[NH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48].[N+:31]([C:22]1[CH:23]=[N:24][C:25]2[C:30]([C:21]=1[NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:29][CH:28]=[CH:27][CH:26]=2)([O-:33])=[O:32]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 6966112-Aminododecanoic AcidHCID 112758084-Chloro-3-nitroquinolineHCID 5744705084636-23-7

Product 2

HCID 5744705084636-23-7HCID 57447051HCID 57447051, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 12-aminododecanoate hydrochloride was prepared from 12-aminododecanoic acid, thionyl chloride, and ethanol by the general method of C. Temple, Jr., R. D. Elliott, and J. A. Montgomery, J. Med. Chem., 1988, 31, 697-700. The general method described in Step 1 of Example 15 was used to react 4-chloro-3-nitroquinoline (15.5 g, 74.4 mmol), ethyl 12-aminododecanoate hydrochloride (25.0 g, 89.3 mmol), and triethylamine (18.8 g, 186 mmol) in dichloromethane for 15 hours to provide ethyl 12-(3-nitroquinolin-4-ylamino)dodecanoate (30.0 g) as a yellow solid that was used directly in the next step without further purification.

Sources & evidence

ORD record
ord-47ab3dfc286d4149a7b83578fdaa7a7a
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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