Water → 6-bromo-1,2,3,4-tetrahydro-2,2-dimethyl-4-Quinolinamine

HRID 20037Notes

Reaction equation

HRID 20037 reaction equation
[N:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[NH:7][C:6]([CH3:16])([CH3:15])[CH2:5]1)=[N+]=[N-].O.C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOC(C)=O>[Br:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:15])([CH3:16])[CH2:5][CH:4]2[NH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 866141294-Azido-6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 673058276-bromo-1,2,3,4-tetrahydro-2,2-dimethyl-4-Quinolinamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-azido-6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (2.29 g, 8.15 mmol), water (6.50 ml, 361 mmol), and THF (20.4 ml, 8.15 mmol) was added triphenylphosphine (2.35 g, 8.96 mmol) in one portion. The resulting mixture was heated to 40 deg C. and stirred overnight. The crude mixture was dissolved with EtOAc and transferred to a sep. funnel containing 0.5 MHCl. The aqueous layer was washed 5×DCM. The aqueous layer was then neutralized with 6N NaOH and washed 3× with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated to provide the desired product. MS m/z: 239 (M−NH2).

Workup

  1. temperatureThe resulting mixture was heated to 40 deg C
  2. additionfunnel containing 0.5 MHCl
  3. washThe aqueous layer was washed 5×DCM
  4. washwashed 3× with EtOAc
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2409dcfe163049e4b8ef9642f3d75801
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Reaction notes

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