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

HRID 2064932Notes

Reaction equation

N#N.[CH3:3][C:4]1([CH2:9][CH2:10][CH2:11][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([CH2:9][CH2:10][CH2:11][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 mixture of 1-[4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-4-nitro-1H-pyrazole (1.80 g, 7.05 mmol), iron powder (1.20 g, 21.26 mmol) and NH4Cl (1.90 g, 35.25 mmol) in a mixture of EtOH (46.0 mL) and water (23.0 mL) was stirred at 75° C. for 30 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (400 mL) was added followed by 1M NaOH (100 mL). The aq. layer was extracted with CH2Cl2 (2×100 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a deep red oil. LC-MS-conditions 02: tR=0.56 min; [M+H]+=226.53. 1H NMR (400 MHz, CDCl3) δ 1.29 (s, 3H), 1.34-1.46 (m, 2H), 1.61-1.70 (m, 2H), 1.77-1.88 (m, 2H), 2.85 (s, 2H), 3.86-3.92 (m, 2H), 3.92-3.96 (m, 2H), 3.99 (t, J=7.3 Hz, 2H), 7.00 (s, 1H), 7.14 (s, 1H).

Workup

filtrationThe reaction mixture was filtered while hot and
concentrationconcentrated under reduced pressure
additionCH2Cl2 (400 mL) was added
extractionThe aq. layer was extracted with CH2Cl2 (2×100 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-4ed3b585752540d2a300de4de9863fb5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

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