Trifluoroacetic acid → 6-Bromo-1,2,3,4-tetrahydro-3-quinolinamine

HRID 1935601Notes

Reaction equation

HRID 1935601 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH:6]([NH:12]C(=O)OC(C)(C)C)[CH2:5]2.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH:6]([NH2:12])[CH2:5]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 17758659tert-Butyl (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

Product 1

HCID 181770896-Bromo-1,2,3,4-tetrahydro-3-quinolinamineYield 220.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-Bromo-1,2,3,4-tetrahydro-3-quinolinyl)carbamic acid, 1,1-dimethylethyl ester (652 mg, 2 mmol) in dichloromethane at RT under argon was added trifluoroacetic acid (1 mL). After 3 hours, the mixture was concentrated. Chloroform (10 mL) was added and concentrated again in vacuo to afford the title compound (1 g), an oil, which was used without further purification. MS; M(+H)+=227.

Workup

  1. concentrationthe mixture was concentrated
  2. additionChloroform (10 mL) was added
  3. concentrationconcentrated again in vacuo

Sources & evidence

ORD record
ord-22b7c889761f4e31b5c5e5a92dd0735a
Source dataset
uspto-grants-2002_05
Patent number
US06387926B1

Reaction notes

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