Ethanolamine → 2-[(2-Fluoro-6-nitrophenyl)amino]ethanol

HRID 603109Notes

Reaction equation

HRID 603109 reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([CH2:14][NH2:15])[OH:13]>C(O)C>[F:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[NH:15][CH2:14][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 813351,2-Difluoro-3-nitrobenzene

Product 1

HCID 114241932-[(2-Fluoro-6-nitrophenyl)amino]ethanolYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3-Difluoronitrobenzene (15 g, 94.3 mmol) is dissolved in 200 mL of ethanol. Ethanolamine (11.4 ml, 188.7 mmol, 2 equiv) is added and the mixture stirred at room temperature overnight (reaction complete by TLC). Ethanol is evaporated and the resulting residue is dissolved in ethyl acetate, washed with water (to eliminate excess ethanolamine), dried over magnesium sulphate, filtered and evaporated to dryness, giving the desired product as a deep orange oil (18.3 g, 97%). This crude material was used for the next step without further purification.

Workup

  1. custom(reaction complete by TLC)
  2. customEthanol is evaporated
  3. dissolutionthe resulting residue is dissolved in ethyl acetate
  4. washwashed with water (to eliminate excess ethanolamine)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-413eeaae7e9f49d3aa03d5b999f9c106
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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