Triethylamine → 8,9-Dimethoxy-3-nitro-5-[2-(N,N-dimethylamino)ethyl]-5H-dibenzo[c,h][1,6]naphthyridin-6-one

HRID 1612038Notes

Reaction equation

HRID 1612038 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[N:14]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[C:15](=[O:27])[C:16]1[C:21](OC)=[C:20]([O:24][CH3:25])[CH:19]=[CH:18][C:17]=1I)([O-:3])=[O:2].C(Cl)(=O)[C:34](Cl)=[O:35].COC1C=C(C(I)=CC=1OC)C(O)=O.[N+](C1C=C2C(=CC=1)N=CC=C2NCCN(C)C)([O-])=O.C(N(CC)CC)C>C(Cl)Cl>[CH3:25][O:24][C:20]1[C:19]([O:35][CH3:34])=[CH:18][C:17]2[C:8]3[C:7](=[C:6]4[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=[CH:12][C:11]4=[N:10][CH:9]=3)[N:14]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[C:15](=[O:27])[C:16]=2[CH:21]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27584222-Iodo-4,5-dimethoxybenzoic acidHCID 22252594N'-(6-Nitroquinolin-4-yl)-N,N-dimethylethane-1,2-diamineHCID 69235419N-(6-Nitroquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-iodo-5,6-dimethoxybenzamide

Product 1

HCID 98023378,9-Dimethoxy-3-nitro-5-[2-(N,N-dimethylamino)ethyl]-5H-dibenzo[c,h][1,6]naphthyridin-6-oneYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(6-Nitroquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-iodo-5,6-dimethoxybenzamide (8c). Oxalyl chloride (1.5 g, 12.0 mmol) was added to a solution of 3,4-dimethoxy-6-iodobenzoic acid (985 mg, 3.2 mmol) in anhydrous methylene chloride (20 mL), and the stirred mixture was refluxed for 3 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was redissolved in 20 mL of anhydrous methylene chloride, and this solution was added to a solution of 7c (700 mg, 2.7 mmol) and triethylamine (2.0 g, 20.0 mmol) in methylene chloride (30 mL), and the resulting mixture was stirred at reflux for 2 hours. The reaction mix was cooled and washed with saturated sodium bicarbonate (3×75 mL), and extracted with 5% aqueous HCl (4×100 mL). The combined aqueous extracts were basified with 30% NaOH and then extracted with chloroform (3×100 mL). Combined organic extracts were then dried (MgSO4) and evaporated to give 1.15 g of the amide, in 78% yield; 1H NMR (CDCl3) δ 2.23 (s, 6H), 2.63 (m, 2H), 3.35 (s, 3H), 3.71 (s, 3H), 3.96 (m, 1H), 4.29 (m, 1H), 6.50 (s, 1H), 6.94 (s, 1H), 7.79 (d, 1H, J=5.2), 8.22 (d, 1H, J=9.2), 8.48 (d, 1H, J=9.2), 9.0 (d, 1H, J=5.2), 9.28 (s, 1H); 13C NMR (CDCl3) δ 45.5, 48.0, 55.6, 56.1, 56.8, 82.3, 110.7, 120.9, 121.5, 122.9, 123.4, 125.5, 132.2, 133.7, 145.9, 148.4, 149.1, 149.8, 151.5, 154.1, 169.7; IR (CHCl3) 1345, 1535, 1655.

Workup

  1. temperaturethe stirred mixture was refluxed for 3 hours
  2. concentrationThe mixture was then concentrated to dryness under reduced pressure
  3. dissolutionThe acid chloride was redissolved in 20 mL of anhydrous methylene chloride
  4. temperatureat reflux for 2 hours
  5. additionThe reaction mix
  6. temperaturewas cooled
  7. washwashed with saturated sodium bicarbonate (3×75 mL)
  8. extractionextracted with 5% aqueous HCl (4×100 mL)
  9. extractionextracted with chloroform (3×100 mL)
  10. dry with materialCombined organic extracts were then dried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-f7804816168249e3a694f10c688ff623
Source dataset
uspto-grants-2006_01
Patent number
US06992089B2

Reaction notes

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