2-Methyl-6-nitroaniline → HCID 86713573, compound

HRID 2404030Notes

Reaction equation

HRID 2404030 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH2:11].[H-].[Na+].Cl[C:15]1[N:24]=[CH:23][C:22]2[N:21]=[C:20]([C:25]3[C:30]([Cl:31])=[C:29]([O:32][CH3:33])[CH:28]=[C:27]([O:34][CH3:35])[C:26]=3[Cl:36])[C:19](=[O:37])[N:18]([CH3:38])[C:17]=2[N:16]=1>CN(C)C=O>[Cl:31][C:30]1[C:29]([O:32][CH3:33])=[CH:28][C:27]([O:34][CH3:35])=[C:26]([Cl:36])[C:25]=1[C:20]1[C:19](=[O:37])[N:18]([CH3:38])[C:17]2[N:16]=[C:15]([NH:11][C:3]3[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[N:24]=[CH:23][C:22]=2[N:21]=1

Participants

5

Reactant 3

HCID 112982-Methyl-6-nitroanilineHCID 24758Sodium hydrideHCID 86713574HCID 86713574, compound

Product 1

HCID 86713573HCID 86713573, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 2-methyl-6-nitrobenzenamine (100 mg, 1 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (53 mg, 1.3 mmol), and the mixture was stirred at RT (10° C.) for 10 mins, followed by the addition of 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)-8-methylpteridin-7(8H)-one (322 mg, 1 mmol). The mixture was stirred at RT (10° C.) for another 30 min and then quenched by water. The precipitate was collected via filtration, washed with cold water and dried to give the title compound (180 mg, 75%) as a yellow powder. MS (ES+) C22H18Cl2N6O5 requires: 516, 518. found: 517, 519 [M+H]+.

Workup

  1. stirringThe mixture was stirred at RT (10° C.) for another 30 min
  2. customquenched by water
  3. filtrationThe precipitate was collected via filtration
  4. washwashed with cold water
  5. customdried

Sources & evidence

ORD record
ord-7512178c40ea486db14d63076a05ae78
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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