4-Bromoaniline → 1-[3-(6-Bromo3-nitroquinolin-4-ylamino)propyl]pyrrolidin-2-one

HRID 9397

Reaction equation

HRID 9397 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2Cl.BrC1C=CC(N)=CC=1.[NH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[O:33]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[NH:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[O:33]

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 219841286-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 219842011-[3-(6-Bromo3-nitroquinolin-4-ylamino)propyl]pyrrolidin-2-oneYield 87.8%

Procedure

6-Bromo-4-chloro-3-nitroquinoline (50.62 g, 177.8 mmol), prepared from 4-bromoaniline according to the methods described in Parts A–D of Example 1, was treated with 1-(3-aminopropyl)pyrrolidin-2-one (27.5 mL, 196 mmol) according to the method described in Part E of Example 1 to provide 61.41 g of 1-[3-(6-bromo-3-nitroquinolin-4-ylamino)propyl]pyrrolidin-2-one as a solid.

Sources & evidence

ORD record
ord-9bc5d76282ce46f99fc9bea711c2f243
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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