Sodium Iodide → 4-(2,4-Dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile

HRID 989363

Reaction equation

HRID 989363 reaction equation
[Cl:1][C:2]1[CH:30]=[C:29]([Cl:31])[C:28]([O:32][CH3:33])=[CH:27][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[C:17]([O:19][CH2:20][CH2:21]Cl)[C:16]([O:23][CH3:24])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:25]#[N:26].[Cl:34][C:35]1[CH:63]=[C:62]([Cl:64])[C:61]([O:65][CH3:66])=[CH:60][C:36]=1[NH:37][C:38]1[C:47]2[C:42](=[CH:43][C:44]3[CH:51]=[C:50]([O:52][CH3:53])[C:49]([O:54][CH2:55][CH2:56]Cl)=[CH:48][C:45]=3[CH:46]=2)[N:41]=[CH:40][C:39]=1[C:58]#[N:59].[CH3:67][N:68]1[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]1.[I-].[Na+]>COCCOC>[Cl:34][C:35]1[CH:63]=[C:62]([Cl:64])[C:61]([O:65][CH3:66])=[CH:60][C:36]=1[NH:37][C:38]1[C:47]2[C:42](=[CH:43][C:44]3[CH:51]=[C:50]([O:52][CH3:53])[C:49]([O:54][CH2:55][CH2:56][N:71]4[CH2:72][CH2:73][N:68]([CH3:67])[CH2:69][CH2:70]4)=[CH:48][C:45]=3[CH:46]=2)[N:41]=[CH:40][C:39]=1[C:58]#[N:59].[Cl:1][C:2]1[CH:30]=[C:29]([Cl:31])[C:28]([O:32][CH3:33])=[CH:27][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[C:17]([O:19][CH2:20][CH2:21][N:71]4[CH2:72][CH2:73][N:68]([CH3:67])[CH2:69][CH2:70]4)[C:16]([O:23][CH3:24])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:25]#[N:26]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 531671-MethylpiperazineHCID 115696394-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrileHCID 116633894-(2,4-Dichloro-5-methoxyanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile

Product 2

HCID 53304294-(2,4-Dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrileHCID 53304384-(2,4-Dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.4 g (0.8 mmol) of 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-(2,4-dichloro-5-methoxyanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture), 1.25 ml (11.27 mmol) of 1-methyl piperazine and 0.05 g of sodium iodide in 2.0 mL of ethylene glycol dimethyl ether is heated at 90° C. for 2 hours under nitrogen. The mixture is cooled, the solvent is removed in vacuo and the resulting residue is stirred with saturated solution of sodium bicarbonate. The crude solid is collected by filtration, washed with water, and dried in vacuo. Purification is carried out by silica gel chromatography, eluting with a gradient of 92:8 to 85:15 methylene chloride/methanol to yield 0.149 g of 4-(2,4-dichloro-5-methoxyanilino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 141-150° C. and 0.203 g of 4-(2,4-dichloro-5-methoxyanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 132-135° C.

Workup

  1. temperatureThe mixture is cooled
  2. customthe solvent is removed in vacuo
  3. filtrationThe crude solid is collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customPurification
  7. washeluting with a gradient of 92:8 to 85:15 methylene chloride/methanol

Sources & evidence

ORD record
ord-131c8c8cf53243acb2200376729c79aa
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Linked notes

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