2-Iodobenzoic acid → N-(6,7-Methylenedioxyquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-iodobenzamide

HRID 1611580Notes

Reaction equation

HRID 1611580 reaction equation
C(Cl)(=O)C(Cl)=O.[I:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[CH2:17]1[O:29][C:28]2[CH:27]=[C:26]3[C:21]([C:22]([NH:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[CH:23][CH:24]=[N:25]3)=[CH:20][C:19]=2[O:18]1.C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:17]1[O:29][C:28]2[CH:27]=[C:26]3[C:21]([C:22]([N:30]([CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])[C:10](=[O:12])[C:9]4[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=4[I:7])=[CH:23][CH:24]=[N:25]3)=[CH:20][C:19]=2[O:18]1

Participants

7

Reactant 4

HCID 69412-Iodobenzoic acidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10923240N'-(6,7-Methylenedioxyquinolin-4-yl)-N,N-dimethylethane-1,2-diamine

Product 1

HCID 10972996N-(6,7-Methylenedioxyquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-iodobenzamideYield 84%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (1.05 g, 8.1 mmol) was added to a solution of o-iodobenzoic acid (0.57 g, 2.3 mmol) in methylene chloride (20 mL) under nitrogen, and the stirred mixture refluxed for 4 h. The mixture was then concentrated to dryness under vacuum. The acid chloride was redissolved in methylene chloride (20 mL) and added to a solution of compound 7 and triethylamine (2.0 g, 20.0 mmol) in methylene chloride (20 mL). The reaction was stirred at reflux under nitrogen for 2 h. The mixture was then cooled and washed with a saturated solution of sodium bicarbonate (3×75 mL), and extracted into dilute HCl (3×75 mL), and the combined aqueous extracts were washed with chloroform (75 mL), made basic using 30% NaOH, then extracted with chloroform (3×75 mL). The combined organic extracts were washed with brine (100 mL), dried (anhydrous MgSO4), and concentrated in vacuo, to give 795 mg, in 84% yield; IR (CHCl3) 1653; 1H NMR (CDCl3) δ 2.23 (s, 6H), 2.60 (m, 2H), 3.52 (m, 1H), 4.57 (m, 1H), 6.13 (d, 1H, J=0.7), 6.16 (d, 1H, J=0.7), 6.78 (m, 3H), 7.32 (m, 2H), 7.36 (s, 1H), 7.64 (d, 1H, J=7.6), 8.48 (d, 1H, J=4.8); 13C NMR (CDCl3) δ 45.6, 46.8, 56.5, 93.9, 98.4, 102.3, 106.5, 120.2, 122.8, 126.5, 127.2, 128.3, 130.2, 139.5, 141.5, 145.6, 148.2, 149.2, 151.2, 170.0.

Workup

  1. temperaturethe stirred mixture refluxed for 4 h
  2. concentrationThe mixture was then concentrated to dryness under vacuum
  3. dissolutionThe acid chloride was redissolved in methylene chloride (20 mL)
  4. temperatureat reflux under nitrogen for 2 h
  5. temperatureThe mixture was then cooled
  6. washwashed with a saturated solution of sodium bicarbonate (3×75 mL)
  7. extractionextracted into dilute HCl (3×75 mL)
  8. washthe combined aqueous extracts were washed with chloroform (75 mL)
  9. extractionextracted with chloroform (3×75 mL)
  10. washThe combined organic extracts were washed with brine (100 mL)
  11. dry with materialdried (anhydrous MgSO4)
  12. concentrationconcentrated in vacuo
  13. customto give 795 mg

Sources & evidence

ORD record
ord-d9eba35a2d4c414097de0bb01c683735
Source dataset
uspto-grants-2006_01
Patent number
US06989387B2

Reaction notes

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