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{2-[6-(ethyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamine → 1-[(Dimethylamino)acetyl]-6-(ethyloxy)-1,2,3,4-tetrahydro-7-quinolinamine

HRID 1014299
Notes
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Reaction equation

HRID 1014299 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[N+:14]([O-])=O)[N:10]([C:17](=[O:22])[CH2:18][N:19]([CH3:21])[CH3:20])[CH2:9][CH2:8][CH2:7]2)[CH3:2].[H][H]>CO.[Pd]>[CH3:21][N:19]([CH2:18][C:17]([N:10]1[C:11]2[C:6](=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[C:13]([NH2:14])[CH:12]=2)[CH2:7][CH2:8][CH2:9]1)=[O:22])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 59441935{2-[6-(ethyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 594421011-[(Dimethylamino)acetyl]-6-(ethyloxy)-1,2,3,4-tetrahydro-7-quinolinamineYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887Methanol
Solvent
2×

Procedure

A solution of {2-[6-(ethyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-2-oxoethyl}dimethylamine (5.8 g, 18.87 mmol) in degassed methanol (50.0 mL) was added to a suspension of 10% Pd/C (3.0 g, 16.36 mmol) in degassed methanol (5 mL) and maintained under a 50 psi hydrogen gas with rapid stirring for 16 hours. The suspension was purged with nitrogen, filtered through celite, all volatiles removed, and the resulting residue was purified by flash column chromatography to afford 1-[(dimethylamino)acetyl]-6-(ethyloxy)-1,2,3,4-tetrahydro-7-quinolinamine (2.85 g, 63%) as a viscous yellow liquid which solidified upon standing for 10 hours. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.80 (s, 1 H), 6.55 (s, 1 H), 4.52 (s, 2 H), 3.95 (q, J=6.89 Hz, 2 H), 3.61 (t, J=6.02 Hz, 2 H), 3.15 (s, 2 H), 2.55 (t, J=6.52 Hz 2 H), 2.20 (s, 6 H), 1.73-1.86 (m, 2 H), 1.32 (t, J=7.02 Hz, 3 H).

Workup

  1. customThe suspension was purged with nitrogen
  2. filtrationfiltered through celite
  3. customall volatiles removed
  4. customthe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-1f8ccc2bb1cd489f846a82fb50f6d8b5
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981903B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes