Dichloromethane → HCID 12547487, compound

HRID 1192855Notes

Reaction equation

HRID 1192855 reaction equation
FC(F)(F)C(O)=O.ClCCl.C(OC([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][C:28]#[N:29])=[CH:21][CH:20]=1)=O)(C)(C)C>>[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][C:28]#[N:29])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57672617HCID 57672617, compound

Product 1

HCID 12547487HCID 12547487, compoundYield 117.5%

Procedure

A 0.25 M solution of trifluoroacetic acid in dichloromethane (5 mL, 1.25 mmol) was added to 4-[4-(t-Butoxycarbonylamino)phenyl]butanenitrile (98) (0.22 g, 0.85 mmol). After 30 min, reaction was quenched with 1 N NaOH solution. The mixture was partitioned with ethyl acetate (30 mL) and water (20 mL). The organic layer was dried over MgSO4, concentrated to give 4-(4-Aminophenyl)butanenitrile (97) (0.16 g, 99%) which was used without further purification.

Workup

  1. customreaction
  2. customwas quenched with 1 N NaOH solution
  3. customThe mixture was partitioned with ethyl acetate (30 mL) and water (20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-90839db4885f4328bf12b150234d3526
Source dataset
uspto-grants-2014_03
Patent number
US08680291B2

Reaction notes

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