N,N-dimethyl-m-phenylenediamine → HCID 5328849, compound

HRID 1935160Notes

Reaction equation

HRID 1935160 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][C:7]([C:15]#[N:16])=[CH:6]2.[CH3:17][N:18]([CH3:26])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1>COCCO>[CH3:17][N:18]([CH3:26])[C:19]1[CH:20]=[C:21]([NH:25][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][C:7]=2[C:15]#[N:16])[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 76084N,N-dimethyl-m-phenylenediamineHCID 11806053HCID 11806053, compound

Product 1

HCID 5328849HCID 5328849, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A 1.25 gram (5 mmole) portion of 4-chloro, 6,7-dimethoxy-quinoline-3-carbonitrile and a 1.05 gram (5 mmole) portion of N,N-dimethyl-1,3-phenylenediamine in 1 ml of 2-methoxyethanol were refluxed for 2 hours in an oil bath at 154 deg. Cooling gave a solid which was recrystallized from water to give 0.4 grams (19%) of 4-(3-Dimethylamino-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile which melted at 246-249° C.: mass spectrum (electrospray m/e): (M+H)=349.2., (M+2H)+2=174.9.

Workup

  1. temperatureCooling
  2. customgave a solid which
  3. customwas recrystallized from water

Sources & evidence

ORD record
ord-89260892b84a4663ac8384a4f086c9ba
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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