Trifluoroacetic acid → 6-Methoxyquinolin-3-amine

HRID 495471Notes

Reaction equation

HRID 495471 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[CH:11]=[C:10]([NH2:20])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][O:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]=[CH:9][C:10]([NH2:20])=[CH:11]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22326880N-tert-butyloxycarbonyl-6-methoxy-3-aminoquinoline

Product 1

HCID 5999396-Methoxyquinolin-3-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-tert-butyloxycarbonyl-6-methoxy-3-aminoquinoline (Step F, 3 g, 0.011 mol) in CH2Cl2 (50 mL) cooled at 0° C. was added TFA (8.4 mL, 0.11 mL). The reaction mixture was warmed to RT and stirred for 8 h. The reaction mixture was concentrated under vacuum. The residue was suspended into MTBE. The yellow solid was filtered off and washed with MTBE. The dry yellow solid was suspended in NaOH 1N and the suspension was stirred for 15 min. The resulting slurry was filtered. The solid was washed with water and dried over P2O5 to give 6-methoxy-3-aminoquinoline as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationThe yellow solid was filtered off
  3. washwashed with MTBE
  4. stirringthe suspension was stirred for 15 min
  5. filtrationThe resulting slurry was filtered
  6. washThe solid was washed with water
  7. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-2ae50e70428f4a12879f6b940baedac9
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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