Ethanol → HCID 57894328, compound

HRID 645320Notes

Reaction equation

HRID 645320 reaction equation
CCO.C1(C)C(S([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[C:18](=[O:32])[C:19]2[CH:24]=[CH:23][C:22]([NH:25]C(=O)C(F)(F)F)=[CH:21][CH:20]=2)(=O)=O)=CC=CC=1.[OH-].[K+]>CCOC(C)=O>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:14]2[NH:13][CH:17]=[CH:16][CH:15]=2)=[O:32])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 86618065HCID 86618065, compound

Product 1

HCID 57894328HCID 57894328, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred EtOH (4 mL) solution containing N-toluenesulfonyl-2-(4-(trifluoroacetylamino)benzoyl)pyrrole (0.500 g, 1.15 mmol), was added 40% KOH solution (2 mL) and the mixture was heated at reflux until thin layer chromatography (TLC) analysis showed complete conversion of the starting material. The resulting solution was cooled to room temperature and diluted with EtOAc (20 mL), and the mixture was evaporated to dryness. The crude product was purified by column chromatography (SiO2, EtOAc:Hexanes) to afford the purified product 2-(4-aminobenzoyl)pyrrole (196 mg, 94% yield). 1H NMR (400 MHz, CD2Cl2, 25° C.) δ 4.19 (bs, 2H), 6.33 (m, 1H), 6.72 (d, 2H), 6.88 (m, 1H), 7.10 (m, 1H), 7.82 (d, 2H), 9.90 (bs, 1H); 13C NMR (100 MHz, CD2Cl2, 25° C.) δ 110.9, 114.2, 118.0, 124.5, 128.5, 131.8, 131.9, 151.3, 183.5; HRMS (EI): m/z 186.0793 (100) {M}+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux until thin layer chromatography (TLC) analysis
  3. customthe mixture was evaporated to dryness
  4. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexanes)

Sources & evidence

ORD record
ord-f653c0e3b3994d8db58afb2f3b206fe1
Source dataset
uspto-grants-2010_04
Patent number
US07704610B2

Reaction notes

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