3-Nitroaniline → HCID 178526635, compound

HRID 1432379Notes

Reaction equation

HRID 1432379 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4](Cl)[N:3]=1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18])([O-:14])=[O:13]>C(O)CCCC.CCOCC>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[N:3]=1

Participants

5

Reactant 2

HCID 74233-NitroanilineHCID 1784188752,6-dichloro-1H-purine

Product 1

HCID 178526635HCID 178526635, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 62761-PentanolSolvent

Procedure

2,6-Dichloro-9H-purine (650 mg, 3.44 mmol) and 3-nitroaniline (1.9 g, 13.76 mmol) were stirred in 1-pentanol (5 mL) at 100° C. for 2 h under N2. The mixture was cooled and diluted with Et2O (40 mL). The precipitate was filtered and washed successively on a sinter with Et2O, PriOH, H2O, 10% aq Na2CO3, H2O, PriOH, and Et2O (2×20 mL each). It was then dried in vacuo to afford the title compound as a lemon-yellow powder (1.01 g, quant.). TLC (9:1 CH2Cl2/MeOH): RF=0.35.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe precipitate was filtered
  3. washwashed successively on a sinter with Et2O, PriOH, H2O, 10% aq Na2CO3, H2O, PriOH, and Et2O (2×20 mL each)
  4. customIt was then dried in vacuo

Sources & evidence

ORD record
ord-82aed85083704817b4b52e845b2723ee
Source dataset
uspto-grants-2009_11
Patent number
US07612079B2

Reaction notes

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