Dimethylamine → HCID 59441761, compound

HRID 1014392Notes

Reaction equation

HRID 1014392 reaction equation
CC1C=C2[C:9](=CC=1[N+]([O-])=O)[NH:8][CH2:7]CC2.C([O-])([O-])=O.[K+].[K+].BrCC(Cl)=O.Br[CH2:27][C:28]([N:30]1[C:39]2[C:34](=[CH:35][C:36]([CH3:43])=[C:37]([N+:40]([O-:42])=[O:41])[CH:38]=2)[CH2:33][CH2:32][CH2:31]1)=[O:29].N(C)C>C1COCC1.O.CCOC(C)=O>[CH3:7][N:8]([CH3:9])[CH2:27][C:28]([N:30]1[C:39]2[C:34](=[CH:35][C:36]([CH3:43])=[C:37]([N+:40]([O-:42])=[O:41])[CH:38]=2)[CH2:33][CH2:32][CH2:31]1)=[O:29]

Participants

9

Reactant 5

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 89602Bromoacetyl chlorideHCID 59442001HCID 59442001, compoundHCID 67317236HCID 67317236, compound

Product 1

HCID 59441761HCID 59441761, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a bright orange solution of 6-methyl-7-nitro-1,2,3,4-tetrahydroquinoline (2 g, 10.41 mmol)—(see Achvlediani, R.; Natsvlishvili, M.; Baberkina, E.; Khachidze, M.; Abesadze, I.; Suvorov, N. Synthesis of 1H-pyrrolo[3,2-g]- and 1H-pyrrolo[2,3-g]quinoline. Izvestiya Akademii Nauk Gruzii, Seriya Khimicheskaya (1996), 22(1-4), 43-47.)—in THF (50 mL) was added K2CO3 (4.31 g, 31.2 mmol). The resulting mixture was cooled to 0° C. and was treated with bromoacetyl chloride (1.040 mL, 12.49 mmol) dropwise. The reaction mixture was stirred for 20 min. EtOAc (100 mL) and water (100 mL) were then added. The organic layer was dried (Na2SO4) and concentrated. The crude 1-(bromoacetyl)-6-methyl-7-nitro-1,2,3,4-tetrahydroquinoline (3.26 g, 10.41 mmol) was dissolved in THF (50mL). A 2M Me2NH solution in THF (50 mL) was added. The resulting slurry was filtered, the solids were rinsed with THF. The filtrate was concentrated onto Celite and purified by silica gel chromatography using 1-10% MeOH (containing 0.2% NH3)/CH2Cl2 to afford as a yellow solid (2.09 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.81-1.97 (m, 2H), 2.24 (s, 6H), 2.47 (s, 3H), 2.80 (t, J=6.89 Hz, 2H), 3.25 (s, 2H), 3.68-6.85 (m, 2H), 7.29 (s, 1H), 8.54 (br s, 1H); ESIMS (M+H)+=278.40.

Workup

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. concentrationconcentrated
  3. filtrationThe resulting slurry was filtered
  4. washthe solids were rinsed with THF
  5. concentrationThe filtrate was concentrated onto Celite
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-2e5d011405c34cbabe86f3e246046614
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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