Nitrogen → 1-[3-(2-Methyl-[1,3]dioxolan-2-yl)-benzyl]-1H-pyrazol-4-ylamine

HRID 2064983Notes

Reaction equation

N#N.[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=2)[CH2:12][N:13]2[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[N:14]2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=2)[CH2:12][N:13]2[CH:17]=[C:16]([NH2:18])[CH:15]=[N:14]2)[O:8][CH2:7][CH2:6][O:5]1

Participants

Conditions

Temperature: 75 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[3-(2-methyl-[1,3]dioxolan-2-yl)-benzyl]-4-nitro-1H-pyrazole (148 mg, 0.51 mmol), iron powder (87 mg, 1.54 mmol) and NH4Cl (138 mg, 2.56 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 75° C. for 2 h. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (20 mL) was added followed by 1N NaOH (20 mL). The aq. layer was extracted with CH2Cl2 (2×20 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a deep red oil. LC-MS-conditions 02: tR=0.65 min; [M+H]+=260.25.

Workup

filtrationThe reaction mixture was filtered while hot and
concentrationconcentrated under reduced pressure
additionCH2Cl2 (20 mL) was added
extractionThe aq. layer was extracted with CH2Cl2 (2×20 mL)
dry with materialextracts were dried over Na2SO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-6eb9fa492b9a40efabbc56806e4366db
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

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