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

HRID 2248086Notes

Reaction equation

HRID 2248086 reaction equation
ClCCl.[NH2:4][CH2:5][C:6]([CH3:9])([OH:8])[CH3:7].Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>C(N(CC)CC)C>[CH3:7][C:6]([OH:8])([CH3:9])[CH2:5][NH:4][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 951022-Propanol, 1-amino-2-methyl-HCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 139583422-Methyl-1-((3-nitroquinolin-4-yl)amino)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 150 mL of dichloromethane, 10 mL of triethylamine and 6.7 g (0.075 mole) of 1-amino-2-methyl-2-propanol was added 10.4 g (0.05 mole) of 4-chloro-3-nitroquinoline. The solution was heated on a steam bath for about one hour then evaporated to remove the solvent. The residue was dissolved in dilute hydrochloric acid and filtered. The filtrate was made basic with concentrated ammonium hydroxide to reprecipitate the product. The product was separated by filtration and recrystallized twice from ethanol to provide the novel yellow solid 2-methyl-1-[(3-nitro-4-quinolinyl)amino]-2-propanol, m.p. 244°-246° C. (dec.). Analysis: Calculated for C13H15N3O3 : %C, 59.8; %H, 5.8; %N, 16.0; Found: %C, 59.8; %H, 5.9; %N 16.1.

Workup

  1. temperatureThe solution was heated on a steam bath for about one hour
  2. customthen evaporated
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in dilute hydrochloric acid
  5. filtrationfiltered
  6. customThe product was separated by filtration
  7. customrecrystallized twice from ethanol

Sources & evidence

ORD record
ord-9dad85ac640947e2afea7c5ff76d98fa
Source dataset
uspto-grants-1991_08
Patent number
US05037986

Reaction notes

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