2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → N-[2-(2-Diethylaminoethylamino)-5-nitro-phenyl]-2-(4-ethoxyphenyl)acetamide

HRID 2074444Notes

Reaction equation

HRID 2074444 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][NH:6][C:7]1[C:8]([NH2:16])=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)[CH3:2].[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>[CH2:17]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[NH:16][C:29](=[O:30])[CH2:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:19][CH3:20])=[CH:23][CH:24]=1)[CH3:18]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 78631Benzeneacetic acid, 4-ethoxy-HCID 98378961-N-[2-(diethylamino)ethyl]-4-nitrobenzene-1,2-diamine

Product 1

HCID 4405038N-[2-(2-Diethylaminoethylamino)-5-nitro-phenyl]-2-(4-ethoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

N1-(2-Diethylamino-ethyl)-4-nitro-benzene-1,2-diamine 4a (0.47 g, 1.863 mmol) was dissolved in anhydrous dichloromethane (110 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. (4-Ethoxy-phenyl)-acetic acid 5 (0.352 g, 1.956 mmol) followed by 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.552 g, 2.235 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 3M ammonium hydroxide solution added to adjust pH to 11-12. 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. Recrystallization of the crude solid from ethyl acetate yielded a yellow powder 6a N-[2-(2-Diethylamino-ethylamino)-5-nitro-phenyl]-2-(4-ethoxy-phenyl)-acetamide. Yield: 0.305 grams (39.5%). 1H NMR (DMSO) δ: 0.94 (t, 6H, J=7.1), 1.31 (t, 3H, J=6.9), 2.50 (m, 4H), 2.59 (t, 2H, J=6.5), 3.26 (m, 2H), 3.55 (s, 2H), 4.02 (q, 2H, J=6.9), 6.21 (br s, 1H), 6.75 (d, 1H, J=9.9), 6.87 (d, 2H, J=8.4), 7.24 (d, 2H, J=8.4), 7.97 (m, 2H), 9.54 (br s, 1H); MS (ESI): 415 (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 3M 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. customRecrystallization of the crude solid from ethyl acetate

Sources & evidence

ORD record
ord-933be93d936e4f0d8e8c54261b540042
Source dataset
uspto-grants-2011_04
Patent number
US07919510B2

Reaction notes

Loading…