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Stannous Chloride → 2-Chloro-4-hydrazinylbenzonitrile hydrochloride

HRID 1085
Notes
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Reaction equation

HRID 1085 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[N:11]([O-])=O.[Na+].Cl[Sn]Cl>C1COCC1.O.Cl>[ClH:10].[Cl:10][C:4]1[CH:3]=[C:2]([NH:1][NH2:11])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 24479Stannous ChlorideHCID 887284-Amino-2-chlorobenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 221118492-Chloro-4-hydrazinylbenzonitrile hydrochloride

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

5 g of 4-amino-2-chlorobenzonitrile and 40 ml of concentrated HCl in 30 ml of THF are mixed at -5° C.; 2.26 g of NaNO2 in 30 ml of water are added and the mixture is left stirring for 2 hours, 30 g of SnCl2 ·2H2O in 30 ml of concentrated HCl are then added and stirring is maintained at -5° C. for 30 minutes.

Workup

  1. waitthe mixture is left
  2. stirringstirring

Sources & evidence

ORD record
ord-951984be58214825afaa7f028775b4b9
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723483

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes
HCID 8028
Tetrahydrofuran
Solvent