Pyridine → HCID 18945265, compound

HRID 399853Notes

Reaction equation

HRID 399853 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]2[CH:16]=[CH:15][CH:14]=[CH:13]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[Br:23][CH2:24][C:25](Br)=[O:26].C(OCC)(=O)C>ClCCl>[Br:23][CH2:24][C:25]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]2[CH:16]=[CH:15][CH:14]=[CH:13]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 61147Bromoacetyl bromideHCID 18945373HCID 18945373, compound

Product 1

HCID 18945265HCID 18945265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 3-amino-5-(pyrrol-1-yl)benzoate (1.0 g) and pyridine (0.41 ml) in dichloromethane (20 ml) was added bromoacetyl bromide (0.44 ml) under ice cooling. After stirring for 6 hours at room temperature, the reaction mixture was poured into the mixture of ethyl acetate and ice-water. The organic layer was successively washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was pulverized from diethyl ether to give methyl 3-bromoacetylamino-5-(pyrrol-1-yl)benzoate (1.51 g).

Workup

  1. washThe organic layer was successively washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-2ca61c1add794c19842d3ee9733e5c95
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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