Triethylamine → HCID 68873567, compound

HRID 2366647Notes

Reaction equation

HRID 2366647 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.[CH2:16]([O:18][C:19](=[O:23])[CH2:20][CH2:21][NH2:22])[CH3:17].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:21][CH2:20][C:19]([O:18][CH2:16][CH3:17])=[O:23])=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 458475beta-Alanine, ethyl ester, hydrochloride2×HCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 68873567HCID 68873567, compoundYield 111.3%

Conditions

Temperature
0 °C

Procedure

4-Chloro-3-nitroquinoline (76.1 g, 365 mmol) was treated with β-alanine ethyl ester hydrochloride (50.0 g, 326 mmol) in the presence of triethylamine (94.5 mL, 678 mmol) and potassium carbonate (37.45 g, 271.2 mmol) according to a modification of the method described in Part A of Example 15. Before the addition of β-alanine ethyl ester hydrochloride, the reaction was cooled to 0° C. After this addition, the reaction was stirred for four hours at ambient temperature and subjected to the work-up procedure to provide 105 g of ethyl N-(3-nitroquinolin-4-yl)-β-alaninate.

Workup

  1. additionAfter this addition

Sources & evidence

ORD record
ord-8f4c620217594c8abccebc11aa7b51c5
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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