N-methylhydroxylamine hydrochloride → HCID 58423904, compound

HRID 1408776Notes

Reaction equation

HRID 1408776 reaction equation
Cl.[CH3:2][NH:3][OH:4].C[O-].[Na+].[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13]/[C:12]/2=[N:25]\[C:26]#[N:27]>CO>[NH2:27][C:26]1[N:3]([CH3:2])[O:4][C:12]2([C:11]3[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=3)[O:15][CH:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13]2)[N:25]=1

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 178511906HCID 178511906, compound

Product 1

HCID 58423904HCID 58423904, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methylhydroxylamine HCl salt (28 mg, 0.326 mmol) in anhydrous MeOH (8 mL) was added NaOMe (25 wt. % in MeOH, 15.83 mg, 0.294 mmol), followed by (E)-N-(6-hydroxy-2-phenylchroman-4-ylidene)cyanamide (86 mg, 0.326 mmol). After stirred 10 minutes, the solvent was removed in vacuum. The residue was dissolved in DCM (15 mL) and filtered, and the solvent was removed in vacuum to give the crude product, which was purified by preparative TLC to give 3′-amino-2′-methyl-2-phenyl-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-6-ol (20 mg, 20%). 1HNMR (CDCl3): 7.30-7.51 (m, 5H), 6.95 (s, 1H), 6.69 (m, 2H), 5.15 (t, 3H), 2.98 (s, 3H), 2.28 (d, 2H), 1.17 (s, 1H).

Workup

  1. customthe solvent was removed in vacuum
  2. dissolutionThe residue was dissolved in DCM (15 mL)
  3. filtrationfiltered
  4. customthe solvent was removed in vacuum
  5. customto give the crude product, which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-9e0f650288b5417aa9d118e00337457a
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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