Toluene → N-tert-butyloxycarbonyl-6-methoxy-3-aminoquinoline

HRID 495470Notes

Reaction equation

HRID 495470 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([NH:13]C(O)=O)=[CH:6]2.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])=CC=1.C[C:35]([OH:38])(C)C.[C:39]1([CH3:45])[CH:44]=CC=C[CH:40]=1>CCOC(C)=O>[C:39]([O:24][C:35]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[C:7]([NH2:13])[CH2:8]1)=[O:38])([CH3:45])([CH3:44])[CH3:40]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 223268136-Methoxy-3-carboxyaminoquinoline

Product 1

HCID 22326880N-tert-butyloxycarbonyl-6-methoxy-3-aminoquinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 6-methoxy-3-carboxyaminoquinoline (Step E, 4.8 g, 0.021 mol) in toluene (109 mL) was added DPPA (5.83 mL, 0.026 mol) followed by TEA (3.6 mL, 0.026 mol). The reaction was stirred at RT for 30 min. t-BuOH (8.22 mL, 0.086 mL) was added then the mixture was heated at reflux for 8 h. The solution was diluted with EtOAc and washed 2× with a saturated solution of NH4Cl and 2× with water. The EtOAc solution was dried over MgSO4 and evaporated. The mixture was purified by flash chromatography using 20% EtOAc/hexane to give N-tert-butyloxycarbonyl-6-methoxy-3-aminoquinoline.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 8 h
  4. washwashed 2× with a saturated solution of NH4Cl and 2× with water
  5. dry with materialThe EtOAc solution was dried over MgSO4
  6. customevaporated
  7. customThe mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-c4c6315a29a34643a09a809c1788a9a0
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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