4-Aminobenzoic Acid → HCID 67132175, compound

HRID 244998Notes

Reaction equation

HRID 244998 reaction equation
C[Si]([C:5]#[N:6])(C)C.[NH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1.[C:17]1(=O)[CH2:20][CH2:19][CH2:18]1>ClCCl>[OH:14][CH2:12][C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:17]2([C:5]#[N:6])[CH2:20][CH2:19][CH2:18]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 14496CyclobutanoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 67132175HCID 67132175, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trimethylsilyl cyanide (0.66 ml, 5 mmol) was added dropwise to a mixture of 4-aminobenzoic acid (0.492 g, 4 mmol) and cyclobutanone (0.35 g, 5 mmol) in dichloromethane (10 ml). The reaction mixture was stirred at room temperature for 6 h and then concentrated under vacuum to obtain a brown liquid which was subjected to chromatography (dichloromethane) to yield 36a (0.677 g, 3.36 mmol, 84%) as a brown solid.

Workup

  1. concentrationconcentrated under vacuum
  2. customto obtain a brown liquid which

Sources & evidence

ORD record
ord-c105290073c340fdb7c0fb051e90e440
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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