Hydrochloric Acid → HCID 24777029, compound

HRID 1364456Notes

Reaction equation

HRID 1364456 reaction equation
[Sn](Cl)Cl.Cl.[F:5][C:6]1[CH:24]=[C:23]([F:25])[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][C:23]([F:25])=[CH:24][C:6]=2[F:5])[C:11]=1[C:12]#[N:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24479Stannous ChlorideHCID 24776912HCID 24776912, compound

Product 1

HCID 24777029HCID 24777029, compoundYield 91.5%

Conditions

Temperature
15 °C

Procedure

To a cooled (15° C.) and stirred solution of tin (II) chloride (0.37 g, 1.65 mmol) and con. hydrochloric acid (2.0 mL) was added a solution of 2-(2,4-difluorophenoxymethyl)-6-nitrobenzonitrile (160.0 mg, 0.55 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 131 mg of 2-amino-6-(2,4-difluorophenoxymethyl)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-ab1b91f807b441d49e1d3e1813658753
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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