Sodium Hydroxide → HCID 16793695, compound

HRID 2233269Notes

Reaction equation

HRID 2233269 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=1[Cl:20])#[N:2].O.O.[Sn](Cl)Cl.[OH-].[Na+]>Cl>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[Cl:20])#[N:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 966782HCID 966782, compound

Product 1

HCID 16793695HCID 16793695, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-(2-Cyanophenyl)-2-chloro-4-nitrobenzamide (1.30 g, 4.04 mmol) was added to a stirred suspension of tin (II) chloride dihydrate (4.42 g, 23 mmol) in hydrochloric acid (52 ml) at 0° C. The reaction was allowed to warm to ambient temperature over 2 hours and aqueous sodium hydroxide was added to take the reaction to pH 10. Extraction of the aqueous layer with dichloromethane (3×50 ml), followed by solvent evaporation in vacuo, yielded N-(2-cyanophenyl)-4-amino-2-chlorobenzamide (0.19 g, 16% yield) as a white solid:

Workup

  1. customthe reaction to pH 10
  2. extractionExtraction of the aqueous layer with dichloromethane (3×50 ml)
  3. customfollowed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-df693414ed654c06bc338b21b3d190d5
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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