N,N'-dimethyl-p-phenylenediamine → 2,N4-Dimethyl-N4-(4-methylamino-phenyl)-quinazoline-4,6-diamine

HRID 1876205Notes

Reaction equation

HRID 1876205 reaction equation
[CH3:1][N:2]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=2)[N:14]=[C:13]([CH3:24])[N:12]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH3:10])=[CH:5][CH:4]=1.ClC1C2C(=CC=C([N+]([O-])=O)C=2)N=C(C)N=1.CNC1C=CC(NC)=CC=1>CC(O)C.Cl>[CH3:24][C:13]1[N:12]=[C:11]([N:2]([CH3:1])[C:3]2[CH:4]=[CH:5][C:6]([NH:9][CH3:10])=[CH:7][CH:8]=2)[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([NH2:21])[CH:19]=2)[N:14]=1

Participants

6

Reactant 3

HCID 68306N,N'-dimethyl-p-phenylenediamineHCID 249038664-Chloro-2-methyl-6-nitroquinazolineHCID 68515327N,N'-Dimethyl-N-(2-methyl-6-nitro-quinazolin-4-yl)-benzene-1,4-diamine

Product 1

HCID 592420662,N4-Dimethyl-N4-(4-methylamino-phenyl)-quinazoline-4,6-diamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

N,N′-Dimethyl-N-(2-methyl-6-nitro-quinazolin-4-yl)-benzene-1,4-diamine: To a mixture of 0.15 g (0.67 mmol) of 4-chloro-2-methyl-6-nitro-quinazoline in i-PrOH (10 mL) and concd HCl (0.2 mL) was added 0.1 g (0.73 mmol) of N,N′-dimethyl-benzene-1,4-diamine, and the mixture was stirred at ambient temperature for 18 hours. The precipitate occurred during the reaction was collected and washed with Et2O to give 0.19 mg of the title compound as the HCl salt. LC-MS (ESI+; 324 ([M+H]+)).

Workup

  1. customwas collected
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-2173f18a3db9412a9ad61a37703160c1
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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