Hydrazine hydrate (1:1) → 1-[(dimethylamino)acetyl]-3,3-dimethyl-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine
Reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2[C:5](=[CH:6][C:7]([N+:13]([O-])=O)=[C:8]([O:11][CH3:12])[CH:9]=2)[N:4]([C:16](=[O:21])[CH2:17][N:18]([CH3:20])[CH3:19])[CH2:3]1.O.NN>[Fe](Cl)(Cl)Cl>[CH3:20][N:18]([CH2:17][C:16]([N:4]1[C:5]2[C:10](=[CH:9][C:8]([O:11][CH3:12])=[C:7]([NH2:13])[CH:6]=2)[C:2]([CH3:22])([CH3:1])[CH2:3]1)=[O:21])[CH3:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A suspension of {2-[3,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}dimethylamine (2.20 g, 7.16 mmol), hydrazine hydrate (2.81 mL, 57.3 mmol), iron(III)chloride (0.232 g, 1.432 mmol), and activated carbon (2 g, 7.16 mmol) was warmed at 65° C. for 16 hours. The solution was filtered while still warm through celite, taken to a residue under reduced pressure, and partitioned between chloroform and saturated sodium bicarbonate. The organic layer was washed with saturated sodium chloride (aq), dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford 1-[(dimethylamino)acetyl]-3,3-dimethyl-5-(methyloxy)-2,3-dihydro-1 H-indol-6-amine (1.41 g, 71% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.49 (s, 1 H), 6.69 (s, 1 H), 4.62 (s, 2 H), 3.82 (s, 2 H), 3.73 (s, 3 H), 3.12 (s, 2 H), 2.23 (s, 6 H), 1.22 (s, 6 H).
Workup
- filtrationThe solution was filtered
- temperaturewhile still warm through celite
- custompartitioned between chloroform and saturated sodium bicarbonate
- washThe organic layer was washed with saturated sodium chloride (aq)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-40a9d93f3a0f4b38bb92d954854784f9
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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