2-(Dimethylamino)ethanol → 4-(2,4-Dichloroanilino)-7-[2-(dimethylamino)ethoxy]benzo[g]quinoline-3-carbonitrile

HRID 989348Notes

Reaction equation

HRID 989348 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:20]#[N:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49]O.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]3[CH:18]=[CH:17][C:16]([O:19][CH2:49][CH2:48][N:47]([CH3:51])[CH3:46])=[CH:15][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:20]#[N:21]

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 219564804-(2,4-Dichloroanilino)-7-hydroxybenzo[g]quinoline-3-carbonitrile

Product 1

HCID 219564584-(2,4-Dichloroanilino)-7-[2-(dimethylamino)ethoxy]benzo[g]quinoline-3-carbonitrileYield 20.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 189.1 mg (0.50 mmol) of 4-(2,4-dichloroanilino)-7-hydroxybenzo[g]quinoline-3-carbonitrile, 207.2 mg (0.79mmol) of triphenylphosphine and 66.9 mg (0.75 mmol) of 2-(dimethylamino)-ethanol in 3.0 mL of anhydrous methylene chloride at 0° C. is added dropwise diethyl azodicarboxylate. The resulting reaction mixture is stirred at room temperature under nitrogen for 2 days. The solvent is concentrated in vacuo and the residue is purified on preparative thin layer chromatography (developing solvent: 9:1 methylene chloride/methanol) to provide 46.3 mg (20.5%) of 4-(2,4-dichloroanilino)-7-[2-(dimethylamino)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 115-117° C.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe solvent is concentrated in vacuo
  3. customthe residue is purified on preparative thin layer chromatography (developing solvent: 9:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-15a2f0092d9d42419a578f7faeccbfef
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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