2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 59799758, compound

HRID 2074454Notes

Reaction equation

HRID 2074454 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][NH:9][C:10]1[C:11]([NH2:19])=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1.[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1)[CH3:21].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>C(Cl)(Cl)Cl>[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([NH:19][C:11]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=2[NH:9][CH2:8][CH2:7][CH:3]2[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])=[O:31])=[CH:25][CH:24]=1)[CH3:21]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 78631Benzeneacetic acid, 4-ethoxy-HCID 59799755HCID 59799755, compound

Product 1

HCID 59799758HCID 59799758, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
35 °C

Procedure

N1-[2-(1-Methyl-pyrrolidin-2-yl)-ethyl]-4-nitro-benzene-1,2-diamine 32 (0.396 g, 1.498 mmol) was dissolved in anhydrous chloroform (20 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. (4-Ethoxy-phenyl)-acetic acid 5 (0.284 g, 1.573 mmol) followed by 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.455 g, 1.841 mmol) are added quickly as solids and resulting solution heated in an oil bath at 35° C. for 18 hours. After cooling to room temperature the solvent was removed under reduced pressure and the resulting residue partitioned between H2O and chloroform and 2M ammonium hydroxide solution added to adjust pH to 10. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with chloroform and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated to afford crude solid. The product was purified using silica gel dry column chromatography with a solvent system of (5% 2M NH3 in methanol/95% dichloromethane) to afford a yellow powder 33 2-(4-Ethoxy-phenyl)-N-{2-[2-(1-methyl-pyrrolidin-2-yl)-ethylamino]-5-nitro-phenyl}-acetamide Yield: 0.115 grams (18.0%). 1H NMR (DMSO) δ: 1.31 (t, 3H, J=7.0), 1.43-1.68 (2×m, 4-5H), 1.78-1.91 (m, 2H), 2.01-2.10 (m, 1H), 2.12-2.19 (m, 1H), 2.22 (s, 3H), 2.89-2.99 (m, 1H), 3.19-3.30 (m, 2H), 3.61 (s, 2H), 4.00 (q, 2H, J=6.9), 6.57 (br, 1H), 6.70 (d, 1H, J=9.1), 6.88 (d, 2H, J=8.4), 7.24 (d, 2H, J=8.6), 7.94 (dd, 1H, J=9.1, 2.6), 7.99 (d, 1H, J=2.5), 9.43 (br s, 1H); MS (ESI): 427 (MH+, 100%).

Workup

  1. customfitted with an condenser
  2. additionare added quickly as solids
  3. customresulting solution
  4. temperatureAfter cooling to room temperature the solvent
  5. customwas removed under reduced pressure
  6. customthe resulting residue partitioned between H2O and chloroform and 2M ammonium hydroxide solution
  7. additionadded
  8. customThe mixture was transferred to a separatory funnel
  9. customthe organic layer collected
  10. extractionThe aqueous layer was further extracted with chloroform
  11. washthe combined organic layers were washed with brine
  12. dry with materialdried over magnesium sulphate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customto afford crude solid
  16. customThe product was purified
  17. dry with materialdry column chromatography with a solvent system of (5% 2M NH3 in methanol/95% dichloromethane)

Sources & evidence

ORD record
ord-cf35fc2dad5e4e51a6e7fc8c63d6388a
Source dataset
uspto-grants-2011_04
Patent number
US07919510B2

Reaction notes

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