Ethyl 4-nitro-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate → Ethyl 4-amino-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate

HRID 847286Notes

Reaction equation

HRID 847286 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([NH:17][C:18](=[O:36])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:21][CH:20]=2)[CH:5]=1)([O-])=O>C(O)C.O1CCCC1.[C].[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([NH:17][C:18](=[O:36])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:21][CH:20]=2)[CH:5]=1

Participants

4

Reactant 1

HCID 15106476Ethyl 4-nitro-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate

Product 1

HCID 15106481Ethyl 4-amino-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetateYield 65.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a mixture of 2.81 g of ethyl 4-nitro-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate obtained in Example 26 in 50 ml of ethanol-tetrahydrofuran (1:1) was added 0.5 g of 10% palladium-carbon. Catalytic reduction was performed at room temperature under normal pressure until absorption of hydrogen was discontinued. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The obtained crystals were washed with isopropyl alcohol to obtain 1.72 g of ethyl 4-amino-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate.

Workup

  1. customCatalytic reduction was performed at room temperature under normal pressure until absorption of hydrogen
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washThe obtained crystals were washed with isopropyl alcohol

Sources & evidence

ORD record
ord-35c3caffc14a48b1bdfffdd8890ce47a
Source dataset
uspto-grants-1992_08
Patent number
US05140046

Reaction notes

Loading…