Hydrochloric Acid → HCID 24777540, compound

HRID 2177049Notes

Reaction equation

HRID 2177049 reaction equation
[Sn](Cl)Cl.Cl.[Cl:5][C:6]1[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=1)[O:9][CH2:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[C:12]=1[C:13]#[N:14].[OH-].[K+]>>[NH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:11]([CH2:10][O:9][C:8]2[CH:22]=[CH:23][CH:24]=[C:6]([Cl:5])[CH:7]=2)[C:12]=1[C:13]#[N:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24479Stannous ChlorideHCID 24777536HCID 24777536, compound

Product 1

HCID 24777540HCID 24777540, compoundYield 42%

Conditions

Temperature
15 °C

Procedure

To a cooled (15° C.) and stirred solution of tin (II) chloride (0.4 g, 1.73 mmol) and cone. hydrochloric acid (1.2 mL) was added a solution of 2-(3-chlorophenoxymethyl)-6-nitrobenzonitrile (100.0 mg, 0.35 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. Purification by silica gel chromatography (dichloromethane) yielded 38 mg of 2-amino-6-(3-chlorophenoxymethyl)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
  7. customPurification by silica gel chromatography (dichloromethane)

Sources & evidence

ORD record
ord-0b9a05b3b5a94ada9ac8a524f84a8ff8
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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