Hydroxylamine → HCID 178485580, compound

HRID 646744Notes

Reaction equation

HRID 646744 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH3:19])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=2)=[CH:6][N:7]=1.[NH2:20][OH:21]>C(O)C.O>[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH3:19])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:20][OH:21])=[NH:15])[CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 68650324HCID 68650324, compound

Product 1

HCID 178485580HCID 178485580, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-Amino-6-(3-cyanophenyl)-N-methylpyrazine-2-carboxamide (155 mg, 0.61 mmol) was suspended in ethanol (2 mL) followed by addition of 50% aqueous hydroxylamine (250 uL, 4.1 mmol) and the mixture was heated to reflux for 30 minutes then allowed to cool to room temperature. The suspension was diluted with water (2 mL) and the solid product collected by filtration and dried in vacuo to give crude 3-amino-N-methyl-6-{3-[(hydroxyamino)(imino)methyl]phenyl}pyrazine-2-carboxamide (125 mg, 72% yield) as a yellow solid which was carried forward without further purification: MS (EI) for C13H15N6O2: 287 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. filtrationthe solid product collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-57db65005a1a48fcb79ee6be7e6cd8f1
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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