Hydrochloric Acid → (4-Methoxybenzyl)hydrazine dihydrochloride

HRID 597853Notes

Reaction equation

HRID 597853 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][NH:9][NH:10]C(OC(C)(C)C)=O)=[CH:6][CH:5]=1>O1CCOCC1>[ClH:1].[ClH:1].[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][NH:9][NH2:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 107533141,1-Dimethylethyl 2-[(4-methoxyphenyl)methyl]hydrazinecarboxylate

Product 1

HCID 22747476(4-Methoxybenzyl)hydrazine dihydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 4 N hydrogen chloride in dioxane (2000 mL, 8.00 mol HCl), add tert-butyl 2-(4-methoxybenzyl)hydrazinecarboxylate (324 g, 1.09 mol) dissolved in a minimal amount of dioxane, slowly over a period of 1 h. A precipitate gradually forms. Allow the solution to stir 16 h at 20±5° C. Collect the solids by filtration. Slurry the solids in heptane (2000 mL) and isolate the solids by filtration. Dry the solids using a nitrogen press to give the title compound (242.3 g, 1.08 mol, 98%). 1H NMR (400 MHz, DMSO-d6) δ 8.2-9.0 (bs, 5H), 7.3-7.4 (d, 2H), 6.8-7.0 (d, 2H), 4.0 (s, 2H), 3.7 (s, 3H).

Workup

  1. customCollect the solids
  2. filtrationby filtration
  3. customisolate the solids
  4. filtrationby filtration
  5. customDry the solids

Sources & evidence

ORD record
ord-f34e2230563a4c58af21ea9555077c17
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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