Potassium Hydroxide → HCID 57894353, compound

HRID 645322Notes

Reaction equation

HRID 645322 reaction equation
C1(C)C(S([N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:23]C(=O)C(F)(F)F)=[CH:18][CH:17]=2)(=O)=O)=CC=CC=1.[OH-].[K+]>CCO>[NH2:23][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([C:11]2[NH:10][CH:14]=[CH:13][CH:12]=2)=[O:30])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86618067HCID 86618067, compound

Product 1

HCID 57894353HCID 57894353, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred EtOH (10 mL) solution containing N-toluenesulfonyl-2-(4-(trifluoroacetylaminomethyl)benzoyl)pyrrole (1.00 g, 2.20 mmol), was added 40% KOH solution (2 mL) and the mixture was heated at reflux until TLC analysis showed complete consumption of the starting material. The reaction mixture was then cooled to room temperature worked up as in Example 7. The crude product was suspended in H2O, filtered and dried to afford the purified product 2-(4-aminomethylbenzoyl)pyrrole (381 mg, 86%). 1H NMR (500 MHz, CD3OD, 25° C.) δ 2.43 (s, 3H), 4.53 (s, 2H), 6.42 (m, 1H), 6.77 (m, 1H), 7.41 (d, 2H), 7.72 (d, 2H), 7.85 (m, 1H), 7.95 (d, 2H), 8.39 (t, 1H); 13C NMR (100 MHz, CD3OD, 25° C.) δ 44.6, 109.7, 119.4, 125.6, 126.5, 128.4, 130.4, 136.8, 146.1, 184.6; HRMS (EI): m/z 200.0940 (100) {M}+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux until TLC analysis
  3. customconsumption of the starting material
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-96ff37a59ba8482cba25f957c158b9ce
Source dataset
uspto-grants-2010_04
Patent number
US07704610B2

Reaction notes

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