2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 59799751, compound

HRID 2074463Notes

Reaction equation

HRID 2074463 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[C:10]([NH2:18])=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH2:4][CH2:3]1.[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=[O:30])=[CH:24][CH:23]=1)[CH3:20].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>ClCCl>[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH:18][C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[NH:8][CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:30])=[CH:24][CH:23]=1)[CH3:20]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 78631Benzeneacetic acid, 4-ethoxy-HCID 55080110HCID 55080110, compound

Product 1

HCID 59799751HCID 59799751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N1-(1-Methyl-piperidin-4-yl)-4-nitro-benzene-1,2-diamine 52 (0.330 g, 1.318 mmol) was dissolved in anhydrous dichloromethane (15 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. (4-Ethoxy-phenyl)-acetic acid 5 (0.249 g, 1.384 mmol) followed by 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.391 g, 1.582 mmol) are added quickly as solids and resulting solution heated to reflux for 14 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. Recrystallization of the crude from ethyl acetate yielded a yellow solid 53 2-(4-Ethoxy-phenyl)-N-[2-(1-methyl-piperidin-4-ylamino)-5-nitro-phenyl]-acetamide. Yield: 0.200 grams (36.8%). 1H NMR (DMSO) δ: 1.31 (t, 3H, J=6.9), 1.41-1.56 (m, 2H), 1.86-1.89 (m, 2H), 1.99-2.07 (m, 2H), 2.17 (s, 3H), 2.69-2.73 (m, 2H), 3.37-3.45 (m, 1H), 3.61 (s, 2H), 4.00 (q, 2H, J=7.0), 5.89 (d, 1H, J=7.5), 6.81 (d, 1H, J=9.3), 6.89 (d, 2H, J=8.4), 7.26 (d, 2H, J=8.3), 7.92 (dd, 1H, J=9.3, 2.3), 8.10 (d, 1H, J=2.3), 9.47 (br s, 1H); MS (ESI): 413 (MH+, 100%).

Workup

  1. customfitted with an condenser
  2. additionare added quickly as solids
  3. customresulting solution
  4. temperatureheated
  5. temperatureto reflux for 14 hours
  6. customwas removed under reduced pressure
  7. customthe resulting residue partitioned between H2O and chloroform and 2M ammonium hydroxide solution
  8. additionadded
  9. customThe mixture was transferred to a separatory funnel
  10. customthe organic layer collected
  11. extractionThe aqueous layer was further extracted with chloroform
  12. washthe combined organic layers were washed with brine
  13. dry with materialdried over magnesium sulphate
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customto afford crude
  17. customRecrystallization of the crude from ethyl acetate

Sources & evidence

ORD record
ord-2c508c09778a4a2db24db58eadd3d992
Source dataset
uspto-grants-2011_04
Patent number
US07919510B2

Reaction notes

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