N-methylhydroxylamine hydrochloride → HCID 58424603, compound

HRID 2096537Notes

Reaction equation

HRID 2096537 reaction equation
Cl.[CH3:2][NH:3][OH:4].C[O-].[Na+].[O:8]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[O:21][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:19]/[C:18]/2=[N:31]/[C:32]#[N:33])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO>[CH3:2][N:3]1[C:32]([NH2:33])=[N:31][C:18]2([C:17]3[C:22](=[CH:23][CH:24]=[C:15]([O:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:16]=3)[O:21][CH:20]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:19]2)[O:4]1

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 178511905HCID 178511905, compound

Product 1

HCID 58424603HCID 58424603, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methylhydroxylamine HCl salt (83.6 mg, 1 mmol) in anhydrous MeOH (11 mL) was added NaOMe (25% in MeOH (Wt. %), 0.2 mL, 0.9 mmol), followed by (Z)—N-(6-phenoxy-2-phenylchroman-4-ylidene)cyanamide (340 mg, 1 mmol). After stirring for 10 min, the solvent was removed in vacuo. The residue was redissolved in DCM (30 mL) The mixture was filter, and the solvent was removed to give the residue, which was purified by column chromatography to give 2′-methyl-6-phenoxy-2-phenyl-2′H-spiro[chroman-4,5′-[1, 2, 4]oxadiazol]-3′-amine (200 mg, 52%). 1H-NMR (CDCl3): 2.41-2.66 (m, 1H), 2.65 (m, 1H), 2.75 (m, 1H), 3.32 (m, 3H), 5.35 (m, 1H), 6.95 (m, 2H), 7.06 (m, 1H), 7.20 (m, 2H), 7.42 (m, 3H), 7.48 (m, 3H), 7.51 (m, 2H).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in DCM (30 mL) The mixture
  3. filtrationwas filter
  4. customthe solvent was removed
  5. customto give the residue, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d07836eef6a3482299f89eea3821c596
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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