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

HRID 415522Notes

Reaction equation

HRID 415522 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.CN(C)C=O.C(N(CC)CC)C.[NH2:28][CH2:29][CH2:30][CH2:31][OH:32]>O>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:28][CH2:29][CH2:30][CH2:31][OH:32])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 866337273-[(2-Chloro-3-nitroquinolin-4-yl)amino]propan-1-olYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,4-Dichloro-3-nitroquinoline (20 g, 81.6 mmol) and N,N-dimethylformamide (DMF, 200 mL) were combined in a 1 L round-bottomed flask and stirred for 5 minutes. Triethylamine (12.5 mL, 89.8 mmol) was added in a single portion. 3-Aminopropan-1-ol (6.9 mL, 89.8 mmol) was added in small portions. The reaction mixture was stirred at ambient temperature for 4 hours. Water (about 700 mL) was added and the reaction mixture was stirred for 30 minutes. A yellow precipitate was isolated by filtration, washed with water (about 1 L), and dried under vacuum overnight to provide 22.5 g of 3-[(2-chloro-3-nitroquinolin-4-yl)amino]propan-1-ol.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 4 hours
  2. stirringthe reaction mixture was stirred for 30 minutes
  3. customA yellow precipitate was isolated by filtration
  4. washwashed with water (about 1 L)
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-a8f2d33ee0c5452aad90ceffb3581de4
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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