Hydroxyamine hydrochloride → HCID 178423388, compound

HRID 222625Notes

Reaction equation

HRID 222625 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-7fbea90617554a5398dada75322df8c5
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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