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

HRID 244807Notes

Reaction equation

HRID 244807 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 was 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 was 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-d993bc2c292c48b7a721c80af4e310a9
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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