Dichloromethane → HCID 50998788, compound

HRID 710498Notes

Reaction equation

HRID 710498 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]#[C:12][Si](C)(C)C)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:11]([C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1)#[CH:12]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 584332772-Nitro-4-[(trimethylsilyl)ethynyl]aniline

Product 1

HCID 50998788HCID 50998788, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Nitro-4-(trimethylsilylethinyl)aniline (3.96 g; 16.9 mmol; 1 eq.) was dissolved in MeOH (50 ml) and CH2Cl2 (50 ml) and treated with K2CO3 (9.33 g; 67.6 mmol; 4 eq.). After stirring at room temperature for 5 h, the mixture was diluted with water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×100 ml). The combined organic layers were dried over Na2SO4, evaporated and the residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient. Yield: 2.06 g (75.1%); MS m/z: 163.4 [M+H]+

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×100 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated
  5. customthe residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient

Sources & evidence

ORD record
ord-e48785f2c7274a899fc58dfd5d9316ce
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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