Hydrochloric Acid → 2-(4-Chloro-3-methoxyphenyl)-2-methylpropanehydrazide hydrochloride

HRID 83933Notes

Reaction equation

HRID 83933 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:21])([CH3:20])[C:9]([NH:11][NH:12]C(OC(C)(C)C)=O)=[O:10])=[CH:4][C:3]=1[O:22][CH3:23].Cl>CCOC(C)=O.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:21])([CH3:20])[C:9]([NH:11][NH2:12])=[O:10])=[CH:4][C:3]=1[O:22][CH3:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66741100Tert-butyl 2-(2-(4-chloro-3-methoxyphenyl)-2-methylpropanoyl)hydrazine carboxylate

Product 1

HCID 667408342-(4-Chloro-3-methoxyphenyl)-2-methylpropanehydrazide hydrochlorideYield 123.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-(2-(4-chloro-3-methoxyphenyl)-2-methylpropanoyl)hydrazine carboxylate (12.63 g, 0.04 mol) in EtOAc (100 mL) at 0° C. was added 2M HCl in Et2O (92 mL). The resulting solution was stirred at room temperature 18 h and concentrated in vacuo. The residue was triturated with Et2O, collected by filtration and dried to give 2-(4-chloro-3-methoxyphenyl)-2-methylpropanehydrazide hydrochloride (6.88 g, 67%) as a white solid. 1H NMR (400 MHz, DMSO) δ 11.64 (s, 1H), 7.41-7.39 (d, 1H), 7.01 (s, 1H), 6.92-6.89 (d, 1H), 3.91 (s, 3H), 1.53 (s, 6H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with Et2O
  3. filtrationcollected by filtration
  4. customdried

Sources & evidence

ORD record
ord-7b5eb7121e034cf4bdd4e736a4cf177a
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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