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N-(2-Hydroxyethyl)ethylenediamine → 2-[2-(4-Nitro-2-methylphenylamino)ethylamino]ethanol

HRID 268552
Notes
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Reaction equation

HRID 268552 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[NH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][OH:18].C([O-])([O-])=O.[K+].[K+].CN1CCCC1=O>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][OH:18])=[C:3]([CH3:11])[CH:4]=1)([O-:10])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 585989282-[2-(4-Nitro-2-methylphenylamino)ethylamino]ethanolYield 77.8%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
60 °C

Procedure

2 g of 4-fluoro-3-methyl nitrobenzene, 1.61 g of 2-(2-aminoethylamino)ethanol and 2.14 g of K2CO3 were added to a solution of 20 ml of N-methylpyrrolidinone. The reaction medium was heated at 60° C. for 7 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 2.4 g of 2-[2-(4-nitro-2-methylphenylamino)ethylamino]ethanol (5) were obtained.

Workup

  1. temperatureafter cooling to room temperature
  2. customThe yellow precipitate formed
  3. filtrationwas filtered off
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-380b56030e494935b169924ff1029747
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07445645B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes