Water → HCID 18945373, compound

HRID 399860Notes

Reaction equation

HRID 399860 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O.C(OCC)(=O)C.O>Cl.CO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 18945355HCID 18945355, compound

Product 1

HCID 18945373HCID 18945373, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of methyl 3-nitro-5-(pyrrol-1-yl)benzoate (35.8 g) in concentrated hydrochloric acid (79 ml) and methanol (73 ml) was added portionwise iron (48.6 g). After stirring for 3.5 hours at room temperature, the reaction mixture was poured into a mixture of ethyl acetate and water and filtered. The organic layer was successively washed with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was pulverized from petroleum ether and diisopropyl ether to give methyl 3-amino-5-(pyrrol-1-yl)benzoate (22.7 g).

Workup

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

Sources & evidence

ORD record
ord-232a73fffc134170a190f58e6d84d458
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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