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

HRID 521250Notes

Reaction equation

HRID 521250 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-d572194d873244ceb0e340cb343ea74f
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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