Hydrazine hydrate (1:1) → HCID 66740370, compound

HRID 1627396Notes

Reaction equation

HRID 1627396 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:18])([CH3:17])[C:12](OCC)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O.[NH2:20][NH2:21]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:18])([CH3:17])[C:12]([NH:20][NH2:21])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 20523075Ethyl 2-(3,4-dimethoxyphenyl)-2-methylpropanoate

Product 1

HCID 66740370HCID 66740370, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-(3,4-dimethoxyphenyl)-2-methylpropanoate (2.84 g, 11.26 mmol) and hydrazine hydrate (7.00 mL, 112.56 mmol) in MeOH (15 mL) was heated at 110° C. in a sealed tube. After 12 h, additional hydrazine hydrate (10 mL) was added to the reaction mixture, which then was heated for additional 6 h. The cooled mixture was concentrated to afford 2-(3,4-dimethoxyphenyl)-2-methylpropanehydrazide (2.75 g, quant) as a liquid. 1H NMR (400 MHz, CDCl3) δ 6.94-6.91 (m, 1H), 6.87-6.81 (m, 2H), 3.88 (s, 3H), 3.87 (s, 3H), 3.69 (br s, 3H), 1.56 (s, 6H).

Workup

  1. temperaturethen was heated for additional 6 h
  2. concentrationThe cooled mixture was concentrated

Sources & evidence

ORD record
ord-171a6e2a549541b089805edb2b9e3b60
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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