4-Fluorobenzoyl chloride → HCID 13487022, compound

HRID 648010Notes

Reaction equation

HRID 648010 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][N:7]2[CH:11]=[CH:12][CH:13]=[C:6]12)=[O:4].[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][N:7]2[C:11]([C:19](=[O:20])[C:18]3[CH:22]=[CH:23][C:15]([F:14])=[CH:16][CH:17]=3)=[CH:12][CH:13]=[C:6]12)=[O:4]

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 10583498HCID 10583498, compound

Product 1

HCID 13487022HCID 13487022, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate (2.0 g., 0.01 moles) in dry xylene (30 ml.) containing 4-fluorobenzoyl chloride (4.5 g., 0.028 moles) is heated at reflux temperature in a nitrogen atmosphere for 20 hours. The solvent is removed in vacuo and the residue is purified by t.l.c. on silica gel using hexane-ethyl acetate (3:1) as the developing solvent. Removal of the solvent gives methyl-3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate which, when crystallized from acetone-hexane exhibits a m.p. of 78°-79° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature in a nitrogen atmosphere for 20 hours
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by t.l.c
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-c417040872004c9cb3f8ceddc3248619
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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