Isobutylamine → (2-Amino-2-methylpropyl)(7-benzyloxy-3-nitroquinolin-4-yl)amine

HRID 2203529Notes

Reaction equation

HRID 2203529 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][CH2:24][C:25]([NH2:28])([CH3:27])[CH3:26].C(N)C(C)C>>[NH2:28][C:25]([CH3:27])([CH3:26])[CH2:24][NH:23][C:13]1[C:12]2[C:17](=[CH:18][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[N:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 3

HCID 6558IsobutylamineHCID 131282-MethylpropylenediamineHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 67050934(2-Amino-2-methylpropyl)(7-benzyloxy-3-nitroquinolin-4-yl)amineYield 73.6%

Procedure

7-Benzyloxy-4-chloro-3-nitroquinoline (14.5 g, 46.0 mmol), prepared as described in Parts A-D of Example 1, was treated according to the general method described in Part E of Example 1. 1,2-Diamino-2-methylpropane (5.29 mL, 50.6 mmol) was used in lieu of isobutylamine. After the work-up, the crude product was passed through a layer of silica gel (eluting sequentially with chloroform and 96:4 chloroform:methanol) to provide 12.4 g of (2-amino-2-methylpropyl)(7-benzyloxy-3-nitroquinolin-4-yl)amine as a yellow solid.

Workup

  1. additionwas treated
  2. washeluting sequentially with chloroform and 96:4 chloroform

Sources & evidence

ORD record
ord-e2479c9fc6d0483b88ceb0a4dc1ec115
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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