Trifluoroacetic acid → HCID 66665326, compound

HRID 474247Notes

Reaction equation

HRID 474247 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:4]=1[O:5][CH2:6][CH2:7][NH:8]C(=O)OC(C)(C)C)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:7][CH2:6][O:5][C:4]1[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86668105HCID 86668105, compound

Product 1

HCID 66665326HCID 66665326, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of tert-butyl (2-(2-cyano-5-nitrophenoxy)ethyl)carbamate (4 g, 13.02 mmol) in DCM (20 mL) was added TFA (10 mL). The reaction mixture was stirred at rt for 60 min. The solvent was removed under reduced pressure and treated with saturated sodium bicarbonate solution (10 mL) and extracted with ethyl acetate (2×25 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to get 2-(2-aminoethoxy)-4-nitrobenzonitrile (2.4 g, 89%) as a yellow solid. LC-MS (M+H)+=208.0. 1H NMR (400 MHz, CDCl3) δ ppm 7.89 (1H, d, J=8.4 Hz), 7.83 (1H, s), 7.76 (1H, d, J=8.4 Hz), 4.23 (2H, t, J=5.2 Hz), 3.22 (2H, t, J=5.2 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiontreated with saturated sodium bicarbonate solution (10 mL)
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1121d58c97a0446086c81cc8a9156a91
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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