Hydrogen Peroxide → 5-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carboxamide

HRID 2424764Notes

Reaction equation

HRID 2424764 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:14])[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[OH:17]O>[OH-].[NH4+]>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:14])[N:5]=[CH:4][C:3]=1[C:15]([NH2:16])=[O:17]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 121505605-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 121517035-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carboxamideYield 84%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of 5-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carbonitrile (1.53 g) in saturated ammonium hydroxide (30 mL) was added 30% hydrogen peroxide solution (6 mL). The reaction stirred for 18 h at ambient temperature and was slowly quenched with 60 mL of a saturated sodium sulfate solution. The aqueous layer was extracted with ethyl acetate, dried with magnesium sulfate, filtered and concentrated. MPLC Biotage chromatography eluting with 2-6% methanol/methylene chloride provided the title compound 1.38 g (84%). 400 MHz 1H NMR (DMSO) δ 7.79 (s, 1 H), 7.42 (m, 1H), 7.25 (d, J=7.5 Hz, 2H), 7.19 (d, J=8.3 Hz, 2 H), 7.03 (t, J=6.2 Hz, 1H), 5.83 (s,2H), 3.76 (s, 3 H); MS: (M+H m/z=233.2).

Workup

  1. customwas slowly quenched with 60 mL of a saturated sodium sulfate solution
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washMPLC Biotage chromatography eluting with 2-6% methanol/methylene chloride

Sources & evidence

ORD record
ord-3816b14b50c24bcd9b2f8dba201c09f3
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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