Water → (3-Methoxy-5-nitrophenyl)methanamine

HRID 2071013Notes

Reaction equation

HRID 2071013 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:20]([CH2:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[C:26]([O:33][CH3:34])[CH:25]=1)=[N+]=[N-].O>C1COCC1>[CH3:34][O:33][C:26]1[CH:25]=[C:24]([CH2:23][NH2:20])[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 811549411-(Azidomethyl)-3-methoxy-5-nitrobenzene

Product 1

HCID 59569909(3-Methoxy-5-nitrophenyl)methanamineYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PPh3 (0.0707 g, 0.27 mmol, 1.1 eq) was added to a stirred solution of 1-(azidomethyl)-3-methoxy-5-nitrobenzene (synthesis described herein) in 5 ml THF. After 5 min 1 ml of water was added, and the reaction was stirred overnight. The solvent was removed in vacuo. The residue was dissolved in EtOAc and extracted with 1N HCl (×1). The aqueous layer was adjusted to pH>8 with 1N NaOH and extracted with EtOAc (×1). This organic fraction was washed with brine (×1) and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo to yield 0.030 g (0.16 mmol, 67% yield) of the product.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. extractionextracted with 1N HCl (×1)
  4. extractionextracted with EtOAc (×1)
  5. washThis organic fraction was washed with brine (×1)
  6. dry with materialdried over Na2SO4
  7. filtrationThe inorganics were filtered off
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8d6c6db50f264e76855e03188d1c1b4c
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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