Diethyl Ether → 2-(4-nitrobenzoyl) pyrrole

HRID 1486368Notes

Reaction equation

HRID 1486368 reaction equation
C[Mg+].[Br-].C(OCC)C.[NH:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[N+:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)([O-:16])=[O:15].[NH4+].[Cl-]>C1COCC1.C(Cl)Cl>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([C:10]2[NH:9][CH:13]=[CH:12][CH:11]=2)=[O:22])=[CH:24][CH:25]=1)([O-:16])=[O:15]

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 8027PyrroleHCID 85024-Nitrobenzoyl chlorideHCID 25517Ammonium ChlorideHCID 178418689HCID 178418689, compound

Product 1

HCID 42684372-(4-nitrobenzoyl) pyrrole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

CH3MgBr (3M) in diethylether (30 mL, 90 mmol) was added by dropwise to the solution of pyrrole (6.95 mL, 100 mmol) in THF (150 mL) at −78° C. and continued for 1 h at r.t. 4-nitrobenzoyl chloride (13 g, 70 mmol) in THF (200 mL) was added by dropwise to the solution and stirring was continued for 3 hours at r.t. The mixture was poured into saturated aqueous NH4Cl, and the precipitate dissolved in DCM and added to the aqueous solution. The organic layer was washed with water, dried over MgSO4 and concentrated under vacuum to give an oily product. Compound 1 was isolated by chromatography on silica gel flash column eluting with EtOAc/Hex to furnish a yellow solid (12.4 g, 81%). 1H-NMR (CDCl3) δ 10.01 (bs, 1H, NH), 8.34 (d, J=8.4, 2H), 8.03 (d, J=8.7, 2H), 7.24 (bs, 1H), 6.86 (bs, 1H), 6.38 (bs, 1H); 13C-NMR (CDCl3) δ 182.51, 149.61, 143.62, 130.57, 129.74, 126.67, 123.55, 120.37, 111.69. ESI-MS m/z (M+H) calc'd: 217.0 found 216.9.

Workup

  1. waitwas continued for 3 hours at r.t
  2. additionadded to the aqueous solution
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customto give an oily product

Sources & evidence

ORD record
ord-52c1cc58574d42a5ac7ebea709ca6fe3
Source dataset
uspto-grants-2016_08
Patent number
US09423396B2

Reaction notes

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