Hydrochloric Acid → HCID 24777543, compound

HRID 1364458Notes

Reaction equation

HRID 1364458 reaction equation
[Sn](Cl)Cl.Cl.[CH3:5][O:6][C:7]1[CH:25]=[CH:24][C:10]([O:11][CH2:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[C:14]=2[C:15]#[N:16])=[CH:9][CH:8]=1.[OH-].[K+]>>[NH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:13]([CH2:12][O:11][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:25][CH:24]=2)[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24479Stannous ChlorideHCID 24777539HCID 24777539, compound

Product 1

HCID 24777543HCID 24777543, compoundYield 73%

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-(4-methoxyphenoxymethyl)-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 (1% methanol in dichloromethane) yielded 65 mg of 2-amino-6-(4-methoxyphenoxymethyl)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 (1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-73bf5eda52ed421bbb2ad82c6b441611
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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