Water → 4-[(3-Nitroquinolin-4-yl)amino]butan-1-ol

HRID 2362491Notes

Reaction equation

HRID 2362491 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].C(N(CC)CC)C.[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27].O>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 121061814-[(3-Nitroquinolin-4-yl)amino]butan-1-olYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-chloro-3-nitroquinoline (100.0 g, 479 mmol) and triethylamine (72.8 g, 719 mmol) in dichloromethane (700 mL) was added dropwise 4-amino-1-butanol (42.7 g, 479 mmol). After the addition was complete, water (500 mL) was added to the reaction mixture to cause the product to precipitate. More water (2 L) was added, and the mixture was stirred overnight and then filtered. The organic solution was dried over sodium sulfate, concentrated under reduced pressure, and combined with the product isolated by filtration to provide 4-(3-nitroquinolin-4-ylamino)butan-1-ol (113 g) as a bright yellow solid.

Workup

  1. additionAfter the addition
  2. customto precipitate
  3. additionMore water (2 L) was added
  4. filtrationfiltered
  5. dry with materialThe organic solution was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customisolated by filtration

Sources & evidence

ORD record
ord-20d7587bf50645f58ee25dcec9d735b8
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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