Sodium Carbonate → 4-(3-Dimethylamino-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile

HRID 1935064Notes

Reaction equation

HRID 1935064 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].Cl.Cl.[CH3:22][N:23]([CH3:31])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O.N1C=CC=CC=1>[CH3:22][N:23]([CH3:31])[C:24]1[CH:25]=[C:26]([NH:30][C:2]2[C:11]3[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])[CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 771241,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 101298981-EthoxyethanolHCID 224666114-Chloro-6,7,8-trimethoxy-3-quinolinecarbonitrile

Product 1

HCID 224665464-(3-Dimethylamino-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrileYield 66.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 0.279 g of 4-chloro-6,7,8-trimethoxy-quinoline-3-carbonitrile, 0.23 g of N,N-dimethyl-l,3-phenylenediamine dihydrochloride, 0.2 ml of pyridine, and 15 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 100 ml of water. To this mixture was added sodium carbonate to pH 9. The product was collected, washed with water, and dried to give 0.251 g of 4-(3-dimethylamino-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile as a solid, mp 142-144° C.; mass spectrum (EI, m/e): M 378.1685.

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5f5a7f83f410419ebc142affdc81e616
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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