Water → HCID 58805191, compound

HRID 1465826Notes

Reaction equation

HRID 1465826 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[N:12]1([NH2:18])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[N:12]1([NH:18][C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:7])[CH:8]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20315N-AminomorpholineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 58805191HCID 58805191, compoundYield 257%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (6.7 g, 40 mmol), morpholin-4-ylamine (10.0 g, 9.8 mmol) and anhydrous potassium carbonate (6.1 g, 44 mmol) in N,N-dimethylacetamide (10 ml) was stirred at 120° C. under nitrogen for 2 days. Sample NMR analysis showed almost complete conversion of the starting material. The resultant mixture was then cooled to room temperature, poured into cold water (100 ml) and stirred vigorously and cooled at 5° C. overnight. The resulting precipitate was collected by filtration, washed well with water then dried on the filter funnel. The resulting solid was slurried in diethyl ether, filtered, washed with additional diethyl ether, dried to afford N1-Morpholin-4-yl-4-nitro-benzene-1,3-diamine (6.0 g, 63%).

Workup

  1. stirringstirred vigorously
  2. temperaturecooled at 5° C. overnight
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed well with water
  5. customthen dried on the filter funnel
  6. filtrationfiltered
  7. washwashed with additional diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-5c0b3987b6da4ff1881d4b61fff8abc5
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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