Dimethylamine → 4-(2-(Dimethylamino)ethoxy)-2-nitroaniline

HRID 415061Notes

Reaction equation

HRID 415061 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1.[CH3:15][NH:16][CH3:17]>C1COCC1>[CH3:15][N:16]([CH3:17])[CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 154854442-(4-Amino-3-nitrophenoxy)ethyl bromide

Product 1

HCID 593493934-(2-(Dimethylamino)ethoxy)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a seal tube was added 4-(2-bromoethoxy)-2-nitroaniline (4.5 g, 17 mmol), THF and 40 mL of 2M dimethylamine in THF. The mixture was heated to 80° C. and was stirred overnight. The suspension was concentrated, and the residue was triturated with ether to give 3.5 g of 4-(2-(dimethylamino)ethoxy)-2-nitroaniline which was used in the next step without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.24 (s, 1H), 6.91 (d, 1H), 6.61 (d, 1H), 5.85 (bs, 2H), 4.04 (t, 2H), 2.78 (t, 2H), 2.27 (s, 6H). MS (EI): 226 (MH+).

Workup

  1. concentrationThe suspension was concentrated
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-a4843592685b41ddbad41df41fbf1978
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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