Hydrochloric Acid → HCID 24777540, compound

HRID 1364471Notes

Reaction equation

HRID 1364471 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 conc. 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-83b2476e3ffc4138a4305159d8b59850
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

Loading…