Dimethylformamide → 7-Amino-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one

HRID 1014376Notes

Reaction equation

HRID 1014376 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-])=O)[NH:9][C:8](=[O:16])[CH2:7][CH2:6]2.CN(C)C=O.[H][H]>C(OCC)(=O)C.CO.[Pd]>[NH2:13][C:12]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:16])[NH:9]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 109440476-Methoxy-7-nitro-1,2,3,4-tetrahydroquinolin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 434499397-Amino-6-methoxy-1,2,3,4-tetrahydroquinolin-2-oneYield 92.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-quinolinone (485 mg, 2.18 mmol) was taken in ethyl acetate (10 mL) and methanol (50 mL). Dimethylformamide (10 mL) was added and the mixture heated to ensure dissolution. 10% palladium on carbon (581 mg, Aldrich) was added and the reaction stirred under 60 psi hydrogen pressure for 16 h. The pressure was released, the reaction vessel evacuated, and back-filled with nitrogen twice. The mixture was filtered through celite and the filtrate was concentrated to provide 7-amino-6-(methyloxy)-3,4-dihydro-2(1H)-quinolinone (387 mg, 2.02 mmol, 92%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.32-2.37 (m, 2 H), 2.66-2.72 (m, 2 H), 3.69 (s, 3 H), 4.63 (s, 2 H), 6.20 (s, 1 H), 6.60 (s, 1 H), 9.70 (s, 1 H); ESIMS (M+H)+=193.

Workup

  1. temperaturethe mixture heated
  2. dissolutiondissolution
  3. customthe reaction vessel evacuated
  4. additionback-filled with nitrogen twice
  5. filtrationThe mixture was filtered through celite
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7a73542a6f284c34af25ce93624afd26
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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