1,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2) → 4-(3-Dimethylamino-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile

HRID 1935073Notes

Reaction equation

HRID 1935073 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=2[O:12][CH3:13])[N:5]=[CH:4][C:3]=1[C:16]#[N:17].Cl.Cl.[CH3:20][N:21]([CH3:29])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1.C(OC(O)C)C>N1C=CC=CC=1>[CH3:20][N:21]([CH3:29])[C:22]1[CH:23]=[C:24]([NH:28][C:2]2[C:11]3[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=3[O:12][CH3:13])[N:5]=[CH:4][C:3]=2[C:16]#[N:17])[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 771241,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 101298981-EthoxyethanolHCID 224665354-Chloro-5,8-dimethoxyquinoline-3-carbonitrile

Product 1

HCID 224667364-(3-Dimethylamino-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrileYield 77.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.148 g of 4-chloro-5,8-dimethoxy-3-quinolinecarbonitrile, 0.146 g of N,N-dimethyl-1,3-phenylenediamine dihydrochloride, 0.2 ml of pyridine, and 5 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. Then the mixture was partitioned between ethyl acetate and saturated sodium chloride solution. The organic layer was dried and concentrated in vacuo. The residue thus obtained was chromatographed on silica gel eluting with ethyl acetate. Solvent was removed from product fractions giving 0.160 g of 4-(3-dimethylamino-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile as a solid, mp 103-105° C.; mass spectrum (EI, m/e): M 348.1588.

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. customThen the mixture was partitioned between ethyl acetate and saturated sodium chloride solution
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue thus obtained
  6. customwas chromatographed on silica gel eluting with ethyl acetate
  7. customSolvent was removed from product fractions

Sources & evidence

ORD record
ord-a7e0e63951aa47a5be042d017d1091fa
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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