Water → HCID 68233052, compound

HRID 1465811Notes

Reaction equation

HRID 1465811 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].[CH3:12][O:13][CH2:14][CH2:15][NH2:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH3:12][O:13][CH2:14][CH2:15][NH:16][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:7])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 68233052HCID 68233052, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (21.6 g, 125 mmol), 2-Methoxy-ethylamine (28.1 g, 375 mmol) and anhydrous potassium carbonate (18.9 g, 137 mmol) in N,N-dimethylacetamide (40 ml) was stirred at 135° C. under nitrogen for 2 days. Sample NMR analysis showed complete conversion of the starting material. The resultant mixture was then cooled to room temperature, poured into cold water and stirred vigorously for 30 minutes 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-(2-methoxy-ethyl)-4-nitro-benzene-1,3-diamine (16 g, 61%) as a yellow-orange powder, and used in the next step without further purification.

Workup

  1. stirringstirred vigorously for 30 minutes The resulting precipitate
  2. filtrationwas collected by filtration
  3. washwashed well with water
  4. customthen dried on the filter funnel
  5. filtrationfiltered
  6. washwashed with additional diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-b5e3412a180f45f499f11f1bfba0e38a
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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