Ethanolamine → 2-((6-Methyl-5-nitropyridin-2-yl)amino)ethanol

HRID 594107Notes

Reaction equation

HRID 594107 reaction equation
Br[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[CH2:12]([CH2:14][NH2:15])[OH:13]>C(O)C>[CH3:8][C:6]1[N:7]=[C:2]([NH:15][CH2:14][CH2:12][OH:13])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 247280146-Bromo-2-methyl-3-nitropyridine

Product 1

HCID 112178252-((6-Methyl-5-nitropyridin-2-yl)amino)ethanolYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-bromo-2-methyl-3-nitropyridine (2 g, 9.22 mmol) was dissolved in ethanol (20 mL) and to this solution was added ethanolamine (1.115 mL, 18.43 mmol). The reaction was left to stir overnight under nitrogen, at room temperature. The reaction was concentrated in vacuo, then diluted with ethyl acetate and saturated sodium bicarbonate solution. The organic phase was separated and washed with saturated sodium bicarbonate and brine, then dried using a hydrophobic frit and concentrated in vacuo to give the title compound as a yellow solid (1.68 g). Crude material used directly in next step, without further purification. LCMS (2 min, formic) Rt 0.60 min, m/z (ES+) 198 (M+H).

Workup

  1. waitThe reaction was left
  2. concentrationThe reaction was concentrated in vacuo
  3. additiondiluted with ethyl acetate and saturated sodium bicarbonate solution
  4. customThe organic phase was separated
  5. washwashed with saturated sodium bicarbonate and brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3c093f525ae4ee4a14fadf76214e9a2
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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