3-Amino-1-propanol → 4-[(3-Hydroxypropyl)amino]-3-nitrobenzonitrile

HRID 590406Notes

Reaction equation

HRID 590406 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][CH2:14][CH2:15][CH2:16][OH:17]>C1COCC1>[OH:17][CH2:16][CH2:15][CH2:14][NH:13][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 223493164-[(3-Hydroxypropyl)amino]-3-nitrobenzonitrileYield 101%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluoro-3-nitrobenzonitrile (10 g, 0.06 mol) in THF (50 mL) was added in portions, via syringe, 3-aminopropanol (5 mL, 0.07 mol) and the mixture was stirred at room temperature. After one hour of reaction the crude mixture was evaporated to dryness and AcOEt was added (300 mL). The organic layer was washed with aqueous sodium bicarbonate (250 mL of a 4% aqueous solution) and the aqueous phase was further extracted with AcOEt (2×100 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulphate, and concentrated under reduced pressure to give the title compound as an orange solid (13.4 g, 99% yield) which was used in the next step without further purification.

Workup

  1. customwas evaporated to dryness and AcOEt
  2. additionwas added (300 mL)
  3. washThe organic layer was washed with aqueous sodium bicarbonate (250 mL of a 4% aqueous solution) and the aqueous phase
  4. extractionwas further extracted with AcOEt (2×100 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26a49d4590f64d2faf958665b95b7e3f
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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