Hydrochloric Acid → (4-Methylbenzyl)hydrazine dihydrochloride

HRID 2400525Notes

Reaction equation

HRID 2400525 reaction equation
C(=[N:4][N:5]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)C(OC(C)(C)C)=O)(C)C.[ClH:21]>C1COCC1>[ClH:21].[ClH:21].[CH3:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][NH:5][NH2:4])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59504758tert-Butyl 2-isopropylidene-1-(4-methylbenzyl)hydrazinecarboxylate2×

Product 1

HCID 45074960(4-Methylbenzyl)hydrazine dihydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mechanically stirred solution of tert-butyl 2-isopropylidene-1-(4-methylbenzyl)hydrazinecarboxylate (crude product from Step 2) in THF (950 mL) and HCl (3N aq., 360 mL) was warmed to reflux. After being stirred for 3 h, the yellow solution was cooled to rt and concentrated to a white solid. The crude material was dried under high vacuum overnight, was suspended in Et2O, and was filtered to provide the title compound as a crystalline white solid (87.8 g, 87% for 2 steps): 1H NMR (300 MHz, d6-DMSO) δ 2.27 (s, 3H), 4.00 (s, 2H), 7.17 (d, 2H), 7.29 (d, 2H).

Workup

  1. concentrationconcentrated to a white solid
  2. dry with materialThe crude material was dried under high vacuum overnight
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-8bd872c9e1dc44ef84810dd1aee4aaad
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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