3-Isopropoxypropylamine → (7-Bromo-3-nitroquinolin-4-yl)-(3-isopropoxypropyl)amine

HRID 909335Notes

Reaction equation

HRID 909335 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH:16]([O:19][CH2:20][CH2:21][CH2:22][NH2:23])([CH3:18])[CH3:17]>ClCCl.C(N(CC)CC)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:23][CH2:22][CH2:21][CH2:20][O:19][CH:16]([CH3:18])[CH3:17])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 761943-IsopropoxypropylamineHCID 219843617-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 67382099(7-Bromo-3-nitroquinolin-4-yl)-(3-isopropoxypropyl)amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

7-Bromo-4-chloro-3-nitroquinoline (40 g) was dissolved in dichloromethane (1.4 L) and triethylamine (23.3 mL). 3-Isopropoxypropylamine (19.3 mL) was added dropwise. After 48 hours, the reaction mixture washed successively with water and saturated aqueous sodium chloride. The organic fraction was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. (7-Bromo-3-nitroquinolin-4-yl)-(3-isopropoxypropyl)amine was isolated as a tan solid (51.2 g).

Workup

  1. washthe reaction mixture washed successively with water and saturated aqueous sodium chloride
  2. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85e9efd977d84d13b8de4372b0307c8c
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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