N-methylhydroxylamine hydrochloride → HCID 58424504, compound

HRID 1408796Notes

Reaction equation

HRID 1408796 reaction equation
Cl.[CH3:2][NH:3][OH:4].CO[Na].[Br:8][C:9]1[CH:28]=[CH:27][C:12]2[O:13]C[CH:15](C3C=CC=CC=3)[CH2:16][C:17](=[N:18][C:19]#[N:20])[C:11]=2[CH:10]=1>CO>[Br:8][C:9]1[CH:10]=[C:11]2[C:17]3([O:4][N:3]([CH3:2])[C:19]([NH2:20])=[N:18]3)[CH2:16][CH2:15][O:13][C:12]2=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 58424178N-(7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)cyanamideHCID 178418582HCID 178418582, compound

Product 1

HCID 58424504HCID 58424504, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-methyl-hydroxylamine hydrochloride (42 mg, 0.5 mmol) in MeOH (10 mL) was added MeONa (0.1 mL, 25% (Wt.) in MeOH), followed by N-(7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)cyanamide (170 mg, 0.5 mmol). After stirred for 10 minutes, the solvent was removed in vacuo. The residue was purified by preparative TLC to give 6-bromo-2′-methyl-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (140 mg, 72%).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-76a6e1f994bf4782ac42fd17b0021043
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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