Water → HCID 67451281, compound

HRID 1465835Notes

Reaction equation

HRID 1465835 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][NH:13][CH2:14][CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[NH2:7][C:6]1[CH:8]=[C:2]([N:13]([CH3:12])[CH2:14][CH2:15][OH:16])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 80162-(Methylamino)ethanolHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 67451281HCID 67451281, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (5 g, 29 mmol), 2-Methylamino-ethanol (7 mL, 87 mmol) and anhydrous potassium carbonate (5.3 g, 38 mmol) in N,N-dimethylacetamide (10 ml) were stirred at 125° C. under nitrogen for 1 day. Sample NMR analysis showed complete conversion of the starting material. The resultant mixture was then cooled to room temperature, poured onto cold water (30 mL), stirred vigorously and incubated at 4° C. overnight. The resulting yellow precipitate was collected by filtration, washed well with water then dried on the filter funnel. This was then slurried in diethyl ether, filtered, washed with additional diethyl ether, dried to afford 2-[(3-Amino-4-nitro-phenyl)-methyl-amino]-ethanol (5.4 g, 88% yield) as a yellow solid and used in the next step without further purification.

Workup

  1. stirringstirred vigorously
  2. waitincubated at 4° C. overnight
  3. filtrationThe resulting yellow 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-4f42fe477a6b431bba5b54212d6fcd90
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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