Hydrazine hydrate (1:1) → tert-butyl (3-amino-1-methyl-1H-pyrazol-4-yl)carbamate

HRID 632760Notes

Reaction equation

HRID 632760 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C:12]1[C:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:15][N:14]([CH3:25])[N:13]=1.O.NN>CO>[NH2:3][C:12]1[C:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:15][N:14]([CH3:25])[N:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131735450tert-butyl (3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-methyl-1H-pyrazol-4-yl)carbamate

Product 1

HCID 125470397tert-butyl (3-amino-1-methyl-1H-pyrazol-4-yl)carbamateYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-methyl-1H-pyrazol-4-yl)carbamate (1.8 g) in methanol (26 mL) was added hydrazine monohydrate (0.38 mL), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.1 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8c5b93f25da64bf582cea5a4225ae95e
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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