Hydroxyamine hydrochloride → HCID 178492422, compound

HRID 245083Notes

Reaction equation

HRID 245083 reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=2)[C:9]#[N:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:17][OH:18].C([O-])(O)=O.[Na+]>CO>[CH:1]1([C:6]2[CH:7]=[C:8]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=2)[C:9]([NH:17][OH:18])=[NH:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 674912332-Cyclopentyl-6-methoxy-isonicotinonitrile

Product 1

HCID 178492422HCID 178492422, compoundYield 113.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-cyclopentyl-6-methoxy-isonicotinonitrile (2.09 g, 10.3 mmol) in methanol (100 mL), hydroxylamine hydrochloride (2.15 g, 31.0 mmol) and NaHCO3 (3.04 g, 36.2 mmol) are added. The mixture is stirred at 60° C. for 18 h before it is filtered and the filtrate is concentrated. The residue is dissolved in EA (300 mL) and washed with water (30 mL). The washings are extracted back with EA (4×100 mL) and DCM (4×100 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried under HV to give the title compound (2.74 g) as a white solid; LC-MS**: tR=0.47 min, [M+1]+=236.24; 1H NMR (D6-DMSO): δ 1.61-1.82 (m, 6H), 1.92-2.01 (m, 2H), 3.04-3.13 (m, 1H), 3.84 (s, 3H), 5.90 (s, 2H), 6.86 (s, 1H), 7.13 (s, 1H), 9.91 (s, 1H).

Workup

  1. filtrationis filtered
  2. concentrationthe filtrate is concentrated
  3. dissolutionThe residue is dissolved in EA (300 mL)
  4. washwashed with water (30 mL)
  5. extractionThe washings are extracted back with EA (4×100 mL) and DCM (4×100 mL)
  6. dry with materialextracts are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under HV

Sources & evidence

ORD record
ord-2286104a866b44e6a54b8c9fcc25bd15
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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