Triethylamine → 10h-Indolo[3,2-b]quinoline-11-carboxylic acid(2-dimethylamino-propyl)amide

HRID 12263

Reaction equation

HRID 12263 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]([C:18]([OH:20])=O)=[C:4]1[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:5]1=[N:6]2.[CH3:21][N:22]([CH3:27])[CH2:23][CH:24]([NH2:26])C.[CH2:28](N(CC)CC)C>O=S(Cl)Cl.C(Cl)Cl>[CH3:21][N:22]([CH3:27])[CH:23]([CH3:28])[CH2:24][NH:26][C:18]([C:3]1[C:2]2[C:7](=[CH:8][CH:9]=[CH:10][CH:1]=2)[N:6]=[C:5]2[C:11]3[C:16]([NH:17][C:4]=12)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 990272-Amino-1-dimethylaminopropaneHCID 1010675710H-Indolo[3,2-b]quinoline-11-carboxylic acid

Product 1

HCID 1145084410h-Indolo[3,2-b]quinoline-11-carboxylic acid(2-dimethylamino-propyl)amideYield 31%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

10H-Indolo[3,2-b]quinoline-11-carboxylic acid (0.2 g, 0.76 mmol) was dissolved in 8 ml of refluxing SOCl2. After 6 hours a clear solution was obtained, and all volatiles were removed in vacuo. The crude acid chloride was suspended in 10 ml of CH2Cl2. A solution of N,N-dimethylproylendiamine (0.1 mL, 0.97 mmol) and triethylamine (1 ml) in 10 ml of CH2Cl2 was added at room temperature, and the mixture was stirred for 14 hours. The organic phase was washed (NaHCO3, brine) and dried (MgSO4). Removal of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10) yielded the desired compound (80 mg, 31%) as a solid. m. p. 188-189° C. 1H-NMR [MeOD,_, ppm]: 8.16 (d, J=7.8 Hz, 1H), 7.92 (m, 2H), 7.35-7.20 (m, 3H), 7.04 (m, 2H), 3.62 (m, 2H, CH2NO), 2.55 (m, 2H, CH2N(CH3)2), 2.29 (s, 6H, N(CH3)2), 1.88 (m, 2H, CHO. MS (EI, m/z) 347 (M++1).

Workup

  1. customAfter 6 hours a clear solution was obtained
  2. customall volatiles were removed in vacuo
  3. washThe organic phase was washed (NaHCO3, brine)
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10)

Sources & evidence

ORD record
ord-35de871dc825411f82857dabd9c55ffb
Source dataset
uspto-grants-2010_06
Patent number
US07728000B2

Linked notes

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