N-methylhydroxylamine hydrochloride → 6-bromo-2'methyl-2-phenyl-2'H-spiro(chroman-4,5'-(1,2,4)oxadiazol)-3'-amine

HRID 2096519Notes

Reaction equation

HRID 2096519 reaction equation
Cl.[CH3:2][NH:3][OH:4].[CH3:5][O-:6].[Na+].[Br:8][C:9]1[CH:10]=[C:11]2C(=[CH:17][CH:18]=1)O[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>[Br:8][C:9]1[CH:10]=[C:11]2[C:12]3([O:4][N:3]([CH3:2])[C:26]([NH2:27])=[N:25]3)[CH2:13][CH:14]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:6][C:5]2=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 178511903HCID 178511903, compound

Product 1

HCID 584237866-bromo-2'methyl-2-phenyl-2'H-spiro(chroman-4,5'-(1,2,4)oxadiazol)-3'-amineYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methylhydroxylamine HCl salt (26 mg, 0.307 mmol) in anhydrous MeOH (10 mL) was added NaOMe (25 wt. % in MeOH, 0.07 mL, 0.276 mmol), followed by (Z)—N-(6-bromo-2-phenylchroman-4-ylidene)cyanamide (100 mg, 0.307 mmol). After stirring for 10 minutes, the solvent was removed in vacuo. The residue was dissolved in DCM (20 mL). The mixture was filtered, and the solvent was removed in vacuo to give 6-bromo-2′methyl-2-phenyl-2′H-spiro(chroman-4,5′-(1,2,4)oxadiazol)-3′-amine (100 mg, 87%), which was used in the next step without further purification.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in DCM (20 mL)
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-01c9e3aeee6b48d6990bb9b2641a6e6f
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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