Morpholine → 2-(2-Morpholinoethoxy)-6-nitroaniline

HRID 415110Notes

Reaction equation

HRID 415110 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:6]=1[NH2:7].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CC(N(C)C)=O>[O:18]1[CH2:19][CH2:20][N:15]([CH2:2][CH2:3][O:4][C:5]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:6]=2[NH2:7])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 111719662-(2-Chloro-ethoxy)-6-nitro-phenylamine

Product 1

HCID 593495682-(2-Morpholinoethoxy)-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

2-(2-Chloroethoxy)-6-nitroaniline (1.9 g, 4.63 mmol), morpholine (0.5 mL) was dissolved in 5 mL of DMA. The mixture was heated at 110° C. in a pressure bottle overnight, and then cooled to room temperature. The reaction mixture was separated between ethyl acetate and water, the combined organic layers were washed with water, brine, dried, and concentrated to get 1.3 g of 2-(2-Morpholinoethoxy)-6-nitroaniline, which was used without any further purification. 1H-NMR (400 MHz, CDCl3): δ 7.78 (d, 1H), 6.95 (d, 1H), 6.72 (b, 2H), 6.61 (dd, 1H), 4.16 (t, 2H), 3.75 (t, 2H), 2.82 (m, 2H), 2.58 (m, 4H), 2.10 (m, 2H). MS (EI): 263 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction mixture was separated between ethyl acetate and water
  3. washthe combined organic layers were washed with water, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5acbcab4f92d4bfab01f4b14c7d008d8
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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