Aniline → HCID 58938487, compound

HRID 1038922Notes

Reaction equation

HRID 1038922 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.C([NH:15][C:16]1[C:21]([C:22](OCC)=[O:23])=[CH:20][N:19]=[CH:18][N:17]=1)(=O)C>C(Cl)Cl>[NH2:15][C:16]1[C:21]([C:22]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:23])=[CH:20][N:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 16682925TrimethylaluminumHCID 58938520HCID 58938520, compound

Product 1

HCID 58938487HCID 58938487, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of aniline (336.0 mg, 3.6 mmol) in 7.5 mL of dry CH2Cl2 was slowly added 2.17 mL of Me3Al (2M solution in hexanes) at RT under N2. After 20 min of stirring compound 22 (301 mg, 1.44 mmol) was added to the reaction mixture as a solution in 2 mL of dry CH2Cl2. The reaction mixture was stirred at RT for 16 h and then quenched with NH4Cl (sat.) followed by extraction into CH2Cl2. The combined organic layers were washed with NaHCO3 (sat.), brine and dried over Na2SO4. The crude material was purified by flash chromatography (CH2Cl2/EtOAc) to yield 75.0 mg of the target compound 23 in 24% yield.

Workup

  1. customat RT
  2. customquenched with NH4Cl (sat.)
  3. extractionfollowed by extraction into CH2Cl2
  4. washThe combined organic layers were washed with NaHCO3 (sat.), brine
  5. dry with materialdried over Na2SO4
  6. customThe crude material was purified by flash chromatography (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-08dae064e7974ce5981de54195ed12f6
Source dataset
uspto-grants-2013_10
Patent number
US08552009B2

Reaction notes

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