Hydroxylamine → CID 21927934

HRID 585539Notes

Reaction equation

HRID 585539 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13].[NH2:14][OH:15]>CO>[OH:15]/[N:14]=[C:12](\[NH2:13])/[CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 219279325-(Pyridin-2-ylamino)pentanenitrile

Product 1

HCID 21927934CID 21927934Yield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

5-(Pyridin-2-ylamino)pentanenitrile (1.00 g; 5.71 mmoles) was dissolved in methanol (10 mL) and hydroxylamine (1.4 mL of a 50% aqueous solution; 22.83 mmoles) was added. The reaction mixture was stirred at 40° C. under nitrogen for 2 days. The solvent was removed under vacuum and the resulting oil was placed under vacuum at 40° C. for 6 hours. The product (1Z)-N′-hydroxy-5-(pyridin-2-ylamino)pentanimidamide (A) (1.16 g; 98%) was obtained as a pale yellow oil. 1H NMR (DMSO-d6) δ 8.68 (1H, s, br), 7.91-7.95 (1H, m), 7.29-7.35 (1H, m), 6.35-6.45 (3H, m), 5.25-5.35 (2H, s, br), 3.15-3.23 (2H, m), 1.97 (2H, t, J=7.5 Hz), 1.45-1.60 (4H, m).

Workup

  1. addition22.83 mmoles) was added
  2. customThe solvent was removed under vacuum
  3. waitthe resulting oil was placed under vacuum at 40° C. for 6 hours

Sources & evidence

ORD record
ord-56a7559e3c7447f195ecf1335c810398
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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