Hydrochloric Acid → 2-Amino-6-(2-iodophenoxymethyl)benzonitrile

HRID 1364473Notes

Reaction equation

HRID 1364473 reaction equation
[Sn](Cl)Cl.Cl.[I:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[O:8][CH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[C:11]=1[C:12]#[N:13].[OH-].[K+]>>[NH2:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:10]([CH2:9][O:8][C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=2[I:5])[C:11]=1[C:12]#[N:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24479Stannous ChlorideHCID 247775372-(2-Iodophenoxymethyl)-6-nitrobenzonitrile

Product 1

HCID 247775412-Amino-6-(2-iodophenoxymethyl)benzonitrileYield 34.6%

Conditions

Temperature
15 °C

Procedure

To a cooled (15° C.) and stirred solution of tin (II) chloride (0.74 g, 3.29 mmol) and con. hydrochloric acid (2.0 mL) was added a solution of 2-(2-iodophenoxymethyl)-6-nitrobenzonitrile (250.0 mg, 0.66 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 80 mg of 2-amino-6-(2-iodophenoxymethyl)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-92a8ffd3946c470ab6326a1cf4ac2142
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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