Triethylamine → HCID 57447051, compound

HRID 2366658Notes

Reaction equation

HRID 2366658 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>Cl.NCCCCCCCCCCCC(OCC)=O>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 112758084-Chloro-3-nitroquinolineHCID 5744705084636-23-7

Product 1

HCID 57447051HCID 57447051, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 5744705084636-23-7Catalyst

Procedure

4-Chloro-3-nitroquinoline (15.52 g, 74.40 mmol) was treated with ethyl 12-aminododecanoate hydrochloride (25.0 g, 89.3 mmol) in the presence of potassium carbonate (10.28 g, 74.38 mmol) and triethylamine (25.9 mL, 186 mmol) according to a modification of the method described in Part A of Example 15. After the reaction was stirred for six hours, an analysis by TLC indicated the presence of starting material, and additional ethyl 12-aminododecanate hydrochloride (1.0 g, 3.6 mmol) was added. The reaction was stirred overnight and subjected to the work-up procedure to provide 31.0 g of ethyl 12-(3-nitroquinolin-4-ylamino)dodecanoate.

Workup

  1. additionwas added
  2. stirringThe reaction was stirred overnight

Sources & evidence

ORD record
ord-590d736ec6444993b631054bf44d226b
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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