Hydroxyamine hydrochloride → HCID 178423388, compound

HRID 536130Notes

Reaction equation

HRID 536130 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21]#[N:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:24][OH:25].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21]([NH:24][OH:25])=[NH:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 58101013HCID 58101013, compound

Product 1

HCID 178423388HCID 178423388, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

The product from Example 11.2 (530 mg, 1.82 mmol) and hydroxylamine hydrochloride (0.549 g, 7.9 mmol) were mixed with ethanol (50 mL). To this stirred solution was added sodium bicarbonate (663 mg, 7.9 mmol) and the mixture was heated at 70° C. for 3 h. The solvent was removed in vacuo and the residue dissolved in a mixed solvent (dichloromethane/ethanol 200 mL:10 mL), washed with water, dried (Na2SO4) and concentrated in vacuo to give the desired compound (472 mg, 80%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in a mixed solvent (dichloromethane/ethanol 200 mL:10 mL)
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d0d6407cb3843ffa7f2db042b4b6d91
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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