Stannous chloride dihydrate → (5-Chloro-4-methyl-2-methoxyphenyl)hydrazine

HRID 1166233Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:10])=[C:4]([NH2:11])[CH:3]=1.[N:12]([O-])=O.[Na+].O.O.Cl[Sn]Cl>>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:10])=[C:4]([NH:11][NH2:12])[CH:3]=1

Participants

Reactant 3

HCID 61436Stannous chloride dihydrate

HCID 229976285-Chloro-2-methoxy-4-methylaniline

HCID 23668193Sodium Nitrite

Product 1

HCID 22997655(5-Chloro-4-methyl-2-methoxyphenyl)hydrazineYield 33.2%

Procedure

The title compound was prepared by the general procedure described above for Preparations 2a-i using 4-chloro-5-methyl-2-aminoanisole (10.26 g), NaNO2 (4.5 g), and SnCl2.2H2O (30 g). Workup gave 3.7 g (33%) of (5-chloro-4-methyl-2-methoxyphenyl)hydrazine.

Workup

customThe title compound was prepared by the general procedure

Sources & evidence

ORD record: ord-d393c0e6beba41adbc5d1fddef29b4bb
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613786B2

Reaction notes

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