Hydrochloric Acid → HCID 66924186, compound

HRID 1364446Notes

Reaction equation

HRID 1364446 reaction equation
[Sn](Cl)Cl.Cl.[Cl:5][C:6]1[CH:24]=[CH:23][C:9]([O:10][CH2:11][C:12]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[C:13]=2[C:14]#[N:15])=[C:8]([CH3:25])[CH:7]=1.[OH-].[K+]>>[NH2:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:12]([CH2:11][O:10][C:9]2[CH:23]=[CH:24][C:6]([Cl:5])=[CH:7][C:8]=2[CH3:25])[C:13]=1[C:14]#[N:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24479Stannous ChlorideHCID 66924105HCID 66924105, compound

Product 1

HCID 66924186HCID 66924186, compoundYield 88%

Conditions

Temperature
15 °C

Procedure

To a cooled (15° C.) and stirred solution of tin (II) chloride (0.56 g, 2.48 mmol) and con. hydrochloric acid (2.0 mL) was added a solution of 2-(4-chloro-2-methylphenoxymethyl)-6-nitrobenzonitrile (150.0 mg, 0.5 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 3 hours. The reaction mixture was poured on to crushed-ice and potassium hydroxide solution, stirred, extracted with dichloromethane, filtered and dried to yield 120 mg of 2-amino-6-(4-chloro-2-methylphenoxymethyl)benzonitrile.

Workup

  1. temperatureThe reaction mixture was slowly warmed to room temperature
  2. additionThe reaction mixture was poured on
  3. stirringstirred
  4. extractionextracted with dichloromethane
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-e058fba922e948b3842bd72eaddeb450
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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