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Stannous Chloride → (3-(Trifluoromethoxy)phenyl)hydrazine hydrochloride

HRID 1528048
Notes
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Reaction equation

HRID 1528048 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].[N:13]([O-])=O.[Na+].[Sn](Cl)[Cl:18]>Cl>[ClH:18].[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[C:6]([NH:7][NH2:13])[CH:8]=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 737533-(Trifluoromethoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 45046393(3-(Trifluoromethoxy)phenyl)hydrazine hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
-5 °C

Procedure

3-(Trifluoromethoxy)aniline (3.68 ml) was dissolved in 6 M hydrochloric acid (71 ml), and an aqueous solution (4.7 ml) of sodium nitrite (2.08 g) was added dropwise over 20 min at −5° C. Tin (II) chloride (1.954 ml) was dissolved in 6 M hydrochloric acid (25 ml), and the solution was cooled to −5° C., and added quickly to the above-mentioned reaction mixture at −5° C. The mixture was stirred at −5° C. for 2 hr, and the precipitated solid was collected by filtration, washed with 0.1M hydrochloric acid, and dried under reduced pressure to give the title compound (2.72 g).

Workup

  1. additionadded quickly to the above-mentioned reaction mixture at −5° C
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with 0.1M hydrochloric acid
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-e83942c2d9274a6ea90ca4b06de6ee16
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090586B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes