Triethylamine → HCID 14986940, compound

HRID 1292473Notes

Reaction equation

HRID 1292473 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][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25]>ClCCl>[CH3:26][C:23]([CH3:27])([NH:22][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])[CH2:24][OH:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 14986940HCID 14986940, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 67.1 g (0.322 mole) of 4-chloro-3-nitroquinoline in 800 mL of dichloromethane was added 54 mL (0.38 mole) of triethylamine and 96 mL (0.96 mole) of 2-amino-2-methyl-1-propanol. The mixture was heated at reflux for one hour, then stirred at about 20° C. for about 16 hours. The mixture was concentrated by evaporation in vacuo and the residue was slurred in 1.5 l of water. The product was separated by filtration and dried to provide solid 2,2-dimethyl-2-[(3-nitro-4-quinolinyl)amino]ethanol. The structural assignment was confirmed by comparison of the nuclear magnetic resonance spectrum to that of a sample which was previously used for elemental analysis. Analysis of earlier sample: Calculated for C13H15 N3O2 : % C, 59.8; % H, 5.8; % N, 16.1; Found % C, 59.9; % H, 5.8; % N, 16.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for one hour
  3. concentrationThe mixture was concentrated by evaporation in vacuo
  4. customThe product was separated by filtration
  5. customdried

Sources & evidence

ORD record
ord-5c456072651f461a9d49a864a7b6dfcc
Source dataset
uspto-grants-1998_05
Patent number
US05756747

Reaction notes

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