Hydrochloric Acid → ethyl 5-(2-chloronicotinoyl)-1H-pyrrole-3-carboxylate

HRID 456631Notes

Reaction equation

HRID 456631 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:11]([O:13][C:14]([C:16]1[CH:20]=[CH:19][NH:18][CH:17]=1)=[O:15])[CH3:12].[Sn](Cl)(Cl)(Cl)Cl.Cl>C1C=CC=CC=1>[CH2:11]([O:13][C:14]([C:16]1[CH:20]=[C:19]([C:4]([C:3]2[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=2)=[O:5])[NH:18][CH:17]=1)=[O:15])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24287Tin tetrachlorideHCID 27745412-Chloronicotinoyl chlorideHCID 13070719Ethyl 1H-pyrrole-3-carboxylate

Product 1

HCID 86592241ethyl 5-(2-chloronicotinoyl)-1H-pyrrole-3-carboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2-chloronicotinoyl chloride (493 mg, 2.8 mmol) in benzene (1 mL) was added to a mixture of 1H-pyrrole-3-carboxylic acid ethyl ester (390 mg, 2.8 mmol) in benzene (3 mL), followed by a dropwise addition of tin (IV) chloride (0.5 mL). The mixture was stirred at room temperature under nitrogen for overnight. The reaction was treated with 2N HCl and extracted with ethyl acetate. The combined ethyl acetate was washed, dried and concentrated to give 390 mg (50%) of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-carboxylic acid ethyl ester as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined ethyl acetate was washed
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4bd90ec4895a4d55963322d29859f2ae
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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