Water → 2-Methyl-1-((3-nitroquinolin-4-yl)amino)propan-2-ol

HRID 1907952Notes

Reaction equation

HRID 1907952 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].[NH2:22][CH2:23][C:24]([CH3:27])([OH:26])[CH3:25].O>CN(C=O)C>[CH3:25][C:24]([OH:26])([CH3:27])[CH2:23][NH:22][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 139583422-Methyl-1-((3-nitroquinolin-4-yl)amino)propan-2-olYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Triethylamine (50.0 mL, 360 mmol) was added to a suspension of 4-chloro-3-nitroquinoline (50.0 g, 240 mmol) in DMF (200 mL), followed by dropwise addition of a solution of 1-amino-2-methyl-propan-2-ol (23.5 g, 264 mmol) in DMF (50 mL). The reaction mixture was stirred overnight at room temperature, then water (500 mL) was added and stirring was continued for 30 minutes. A solid was isolated by filtration, washed with water, and dried to yield 60.9 g of 2-methyl-1-[(3-nitroquinolin-4-yl)amino]propan-2-ol, which was used without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes
  3. customA solid was isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-06ee3afbd0cf4494b690defcb115cf77
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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