Trifluoroacetic acid → (4-Aminonaphthalen-1-yloxy)-acetonitrile

HRID 1641289Notes

Reaction equation

HRID 1641289 reaction equation
C(OC(=O)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]#[N:21])=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O.C(OCC)(=O)C>ClCCl>[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]#[N:21])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 59553417(4-Cyanomethoxynaphthalen-1-yl)-carbamic acid tert-butyl ester

Product 1

HCID 59553077(4-Aminonaphthalen-1-yloxy)-acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-cyanomethoxynaphthalen-1-yl)-carbamic acid tert-butyl ester (1.13 g, 3.8 mmol) in anhydrous dichloromethane (15 ml) at room temperature is added trifluoroacetic acid (5 ml). After 4 hours the mixture is poured into ethyl acetate (100 ml) and washed with saturated sodium bicarbonate solution (150 ml). The organic layer is then dried over anhydrous sodium sulfate and evaporated to dryness to give (4-aminonaphthalen-1-yloxy)-acetonitrile as a red brown solid.

Workup

  1. washwashed with saturated sodium bicarbonate solution (150 ml)
  2. dry with materialThe organic layer is then dried over anhydrous sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-57af0d104b0849d989e0c18f38e76dab
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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