Hydrazine hydrate (1:1) → 2-[(Dimethylamino)acetyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine
Reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][C:4]([N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([N+:18]([O-])=O)=[C:11]([O:16][CH3:17])[CH:12]=2)[CH2:7]1)=[O:5].O.NN>[Fe](Cl)(Cl)Cl.CO>[CH3:21][N:2]([CH2:3][C:4]([N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([NH2:18])=[C:11]([O:16][CH3:17])[CH:12]=2)[CH2:7]1)=[O:5])[CH3:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A suspension of N,N-dimethyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-2-oxoethanamine (0.9 g, 3.07 mmol), hydrazine hydrate (0.67 mL, 21.5 mmol), iron(III)chloride (0.125 g, 0.77 mmol), activated carbon (1 g), and methanol (100 mL) was maintained at 65° C. for 12 hours, cooled, and filtered through celite (rinsed with additional methanol). Filtrates were concentrated, redissolved in ethyl acetate, and washed twice with saturated aqueous sodium chloride and sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered, and concentrated to afford 2-[(dimethylamino)acetyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine (0.214 g, 26%) as a white solid. 1H NMR/80° C. (400 MHz, DMSO-d6) δ ppm 6.56 (s, 1 H), 6.41 (s, 1 H), 4.49 (s, 2 H), 4.38 (s, 2 H), 3.73 (3.64 (s, 2 H), 3.11 (s, 2 H), 2.66 (s, 2 H), 2.20 (s, 6 H).
Workup
- temperaturecooled
- filtrationfiltered through celite (rinsed with additional methanol)
- concentrationFiltrates were concentrated
- dissolutionredissolved in ethyl acetate
- washwashed twice with saturated aqueous sodium chloride and sodium bicarbonate
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a874cc1b44744c5d88a7cd8d1aa35af9
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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