Water → HCID 9899728, compound

HRID 1465830Notes

Reaction equation

HRID 1465830 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[CH:17]=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[C:20]([CH:22]=1)[NH2:21].O>CN(C)C(=O)C>[CH3:1][C@H:2]1[CH2:3][N:4]([C:16]2[CH:17]=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[C:20]([CH:22]=2)[NH2:21])[CH2:5][C@@H:6]([CH3:8])[O:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 9899728HCID 9899728, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of cis-2,6-dimethylmorpholine (4.15 g, 36.0 mmol, 1.8 eq) in dry N,N-dimethylacetamide (35 ml) was added potassium carbonate (2.94 g, 21.2 mmol, 1.05 eq) followed by 5-chloro-2-nitroaniline (3.44 g, 19.9 mmol) and the mixture heated in a 120° C. oil-bath under nitrogen for 46 h. The reaction mixture was then cooled to room temperature, poured into water (200 ml) and stirred for 1 h. The suspension was filtered and the collected solid washed carefully with water (3×30 ml), then diethyl ether (2×20 ml) before drying under vacuum over P2O5 to give 5-(cis-2′,6′-dimethylmorpholino)-2-nitroaniline (3.67 g, 73%) as a light ochre powder.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. filtrationThe suspension was filtered
  3. washthe collected solid washed carefully with water (3×30 ml)
  4. dry with materialdiethyl ether (2×20 ml) before drying under vacuum over P2O5

Sources & evidence

ORD record
ord-d7b51bc7fa7a4024b332b555fc84dc7e
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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