4-Chloroaniline → HCID 57435166, compound

HRID 1434821Notes

Reaction equation

HRID 1434821 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([CH:11]=O)[CH:10]=1)=[O:5])[CH3:2].[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C([BH3-])#N.[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.CO>[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([CH2:11][NH:18][C:17]2[CH:19]=[CH:20][C:14]([Cl:13])=[CH:15][CH:16]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 11430Potassium CarbonateHCID 321486Ethyl 4-formyl-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 57435166HCID 57435166, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

0.5052 g (3.02 mmol) of 4-formyl-1H-pyrrole-2-carboxylic acid ethyl ester was dissolved in 12.0 mL (0.25 M) of 5% acetic acid in methanol. 4-chloroaniline (0.4633 g, 3.63 mmol) was added, and the reaction was stirred at room temperature under nitrogen for 30 minutes, then sodium cyanoborohydride (0.3013 g, 4.79 mmol) was added slowly and the reaction was allowed to stir at room temperature overnight. About 5 mL of saturated K2CO3 were added, and the reaction was extracted twice with ethyl acetate. The combined organics were washed with saturated NaHCO3 (˜6 mL) and brine (˜6 mL), then the combined organics were dried with Na2SO4, filtered and concentrated en vacuo. The crude product was purified by silica gel chromatography (Combiflash column, 85:15 Hexanes:Ethyl acetate) to obtain 0.5806 g (69%) of 4-[(4-chlorophenylamino)methyl]-1H-pyrrole-2-carboxylic acid ethyl ester (187) as a light tan solid. Note: Starting material 4-formyl-1H-pyrrole-2-carboxylic acid ethyl ester has an HPLC retention time=7.337 min. HPLC: 8.543 min.

Workup

  1. stirringto stir at room temperature overnight
  2. extractionthe reaction was extracted twice with ethyl acetate
  3. washThe combined organics were washed with saturated NaHCO3 (˜6 mL) and brine (˜6 mL)
  4. dry with materialthe combined organics were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated en vacuo
  7. customThe crude product was purified by silica gel chromatography (Combiflash column, 85:15 Hexanes:Ethyl acetate)

Sources & evidence

ORD record
ord-20f37bf71b474db7bf3c98739befe81a
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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