Water → 3-[(2-Chloro-3-nitroquinolin-4-yl)amino]propan-1-ol

HRID 388608Notes

Reaction equation

HRID 388608 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[NH2:23][CH2:24][CH2:25][CH2:26][OH:27].O>CN(C=O)C>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 866337273-[(2-Chloro-3-nitroquinolin-4-yl)amino]propan-1-olYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4-dichloro-3-nitroquinoline (32 g, 130 mmol) in DMF (100 mL) was cooled to 0° C. Triethylamine (27.5 mL, 198 mmol) was added, and 3-amino-1-propanol (11.9 g, 158 mmol) was slowly added. The reaction was stirred for two hours at room temperature and cooled again to 0° C. Water (300 mL) was added, and the mixture was stirred for 30 minutes at 0° C. A solid was present and was isolated by filtration, washed with water, and dried overnight in a vacuum oven to provide 34.5 g of 3-[(2-chloro-3-nitroquinolin-4-yl)amino]propan-1-ol as a yellow and orange solid.

Workup

  1. temperaturecooled again to 0° C
  2. stirringthe mixture was stirred for 30 minutes at 0° C
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-32915cbbf0c04ddba6f98e5bb1de7d15
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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